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All 27 posts Subject: One pot synthesis of 4-methylaminorex Please login to post Down

Bandil
(you can always take some more)
09-12-03 08:23
No 458588
      One pot synthesis of 4-methylaminorex
(Rated as: excellent)

Hi!

Further exploration of an initial suggestion by Rhodium - to perform both the preparation of the carbamoyl norephedrine as well as its cyclization to trans-4-MAR in one pot gave the following results:

Theory:
When the initial norephedrine hydrochloride is mixed with potassion cyanate, it forms the carbamoyl coumpound in near quantitatie yeilds with respect to the norephedrine. The original patent's uses a slight molar excess of the cyanate in order to give complete conversion. When the first reaction is done, there should thus be a mixture of: N-carbamoyl-norephedrine, potassiumchloride and traces of of cyanate. The remaining cyanate will be destroyed by the huge excess of acid which will be added later. In the end these impurities should have no influence of the ring formation, catalysed by the acid. It should in theory be possible to do the initial reaction and simply add the acid in one portion while heating continusouly till the reaction is over. With this in mind, it seems kind of a waste to isolate the intermediate, so this has to be tested :)

Practice:(in theory of course)
5 grammes of norephedrine.HCl(26,5 mmoles), was placed in a 100 mL FBF, and 2,3 grammes of KOCN(28,4 mmoles) and 25 mL's of distilled water was immediately added in succession. This was heated to reflux directly on the hotplate for two hours.

After this time, 30 mL's of 2M HCl(60 mmoles) was added. This caused a bit of bubbling(probably from the excess cyanate being broken down to gasseus -i-cant-remember-what-). Reflux was continued for an additional two hours. The mixture took on an ever so slight pinkish tint, which the "old" synth also tend to do at this stage.

After 2½ hours of reflux, the mixture was cooled and basified with sodium carbonate and presto a lot of pretty white crystals precipitated on the bottom of the beaker. The yeild looked like that which is expected from the normal reaction. They will be measured shortly.

Conclusion
Total success!!
We'll the usual cyanate route to 4-methylaminorex was easy, but this is more like baking a shake-n-bake cake really ;)(which is VERY easy if you didn't know). Bioassay's are pending though, but nothing that was put into the flask would have reacted the way, the final product did. The yeild will also be measured shortly!

Have a nice and productive weekend!

Kind Regards
Bandil

You can always take some more!

Megatherium
(Hive Bee)
09-12-03 13:35
No 458655
      This caused a bit of bubbling(probably from...

This caused a bit of bubbling(probably from the excess cyanate being broken down to gasseus -i-cant-remember-what-).

The isocyanic acid hydrolyzes to NH₃ and CO₂.

Congrats, what a beautifull procedure blush smile .

Chimimanie
(Hive Bee)
09-14-03 03:40
No 458952
User Picture       Welldone!

What a breakthrough!

Look so easy! Very very nice!

Thank you for the good work (altough were i live E4Euh is illegal frown ), but still!

I cant wait the final yield! cool

Rhodium
(Chief Bee)
09-16-03 19:25
No 459441
User Picture       (4-Methyl)Aminorex related forensic article
(Rated as: good read)

Appearance of Aminorex as a Designer Analog of 4-Methylaminorex
Marcus E. Brewster and Frank T. Davis
Journal of Forensic Sciences 36(2), 587-592 (1991) (https://www.rhodium.ws/chemistry/aminorex.html)

Abstract

A case in which aminorex (cis (±)-4,5-dihydro-5-phenyl-2-oxazolamine) was prepared as a "designer" analog of a controlled substance, methylaminorex (cis-(±)-4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine) is described. The confiscated drug sample was analyzed by high-field (300-MHz) proton nuclear magnetic resonance (NMR) and carbon-13 NMR spectroscopy, as well as electron impact mass spectrometry (70 eV). These examinations proved conclusively that the material in question was aminorex.

Bandil
(you can always take some more)
09-19-03 17:41
No 459973
      Final yield

The final yield has now been measured: 77% mole wise from the PPA.HCl

From 5,0 grammes of PPA.HCl there where prepared 3,6 grammes of 4-methylaminorex freebase with the new method. Compared to the 3,4-dimethylaminorex synthesis from J Chem Soc, 850-854 (1952), it's at least as high as they get, if not higher(i don't have their article lying around, so it's from my clouded memory). This could be attribited to the fact that no collection of the intermediate product is required.

All in all, it's not to shabby if i may say so wink
Regards
Bandil

You can always take some more!

Rhodium
(Chief Bee)
09-19-03 18:36
No 459975
User Picture       4-MAR mentioned in a blog

I just wanted to say that I found someones blog with some comments about 4-MAR (http://www.sixthseal.com/000478.html)

Same blog, a few days later - Arguments for 4-MAR (http://www.sixthseal.com/000479.html)

Glacial_Refluxer
10-15-03 00:33
      Too bad norephedrine hydrochloride / potassium
(Rated as: misinforming)

Vitus_Verdegast
(Hive Bee)
10-15-03 00:42
No 464652
User Picture       How can you speak for most bees?

I do agree that norephedrine is harder to obtain, but there is always synthesis (eg. synth the benzaldehyde and nitroethane yourself) and pill extraction for some countries.

But for KOCN you are *definately* talking outta your ass!
UTFSE!

A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html)

Glacial_Refluxer
(Hive Bee)
10-16-03 19:54
No 465026
User Picture       Potassium ferricyanide and potassium ...

Potassium ferricyanide and potassium thiocyanate are easy
to obtain, will they work here?

http://www.altavista.com/

Rhodium
(Chief Bee)
10-16-03 21:06
No 465040
User Picture       UTFSE

That question has already been asked: Post 455750 (placebo: "If one had a choice between...", Methods Discourse) ...and replied to: Post 455759 (Rhodium: "All three are wrong, unfortunately.", Methods Discourse)

BottlenecksGhost
(Stranger)
10-26-03 12:42
No 466843
      Hmm...

You could be quite mistaken on this one, Rhodium.

In the original patent on McNeil Labs 4-methylaminorex Patent GB1021012, page 3, they suggest potassium thiocyanate instead of an alkali cyanate and using this for the ring-closure in an equivalent manner to the normal cyanate-route.

In this fascinating little patent, the norephedrine+cyanate+acid method which Bandil, Prometheuz and I thought we had been the first to discover is also suggested.

Glacial_Refluxer
(Hive Bee)
10-28-03 08:19
No 467236
User Picture       thiocyanate worked

Swim did not have any luck finding potassium cyanate so he
purchased a small amount of potassium thiocyanate, did a
small scale rxn assumeing failure. Seeing the rxn take on
the pinkish tone surely put a smile on swim's face.

Reality?

SPISSHAK
(Hive Addict)
10-30-03 07:12
No 467763
      interesting so

the oxygen on the oxazoline ring could have possibly been substituted by sulfur.
Find a guinee pig and try to elucidate the pharmcodynamics of this.

Nitroxamide
(Stranger)
10-30-03 20:19
No 467848
      cyanate preparation

Cyanates are easy to prepare. Simply heat an alkali hydroxide with urea.

NaOH + CO(NH2)2 ----> NaOCN + H2O + NH3

Plutonium is a necessary ingredient in the recipe for nirvana.

Glacial_Refluxer
(Hive Bee)
11-28-03 14:55
No 473639
User Picture       4-MTAR?

Anyone think that useing the thiocyanate would create
something like 4-Methyl-Thio-Amino-Rex?

Ive heard of 4-MTA [methyl-thio-amphetamine] a
non-nerotoxic seratonin realeaser so....

I wonder if the thio is not a good thing?

MTMA hmmmm

Rhodium
(Chief Bee)
11-28-03 16:16
No 473643
User Picture       That is completely flawed reasoning

If you look at the structure of 4-Methylthio-Amphetamine and 4-Methylaminorex, you will see that their structures are completely different and that the 4-substituent resides in different parts of their structures.

SilverSurfer
(Hive Bee)
11-30-03 19:08
No 473928
      amazing

Would Phenyl-1-Hydroxy-2-ethanamine work,
Is benzaldehyde + Nitromethane yielding the Hydroxynitroalkan instead of Nitrostyrene possible?
Could the 1-Hydroxyamine be obtained from reduction of nitrostyrene in any way?
Post 404813 (GC_MS: "benzaldehydes + nitromethane pt 1", Methods Discourse)

The only purpose of your life may be to serve as a warning to others http://www.despair.com

Rhodium
(Chief Bee)
11-30-03 21:56
No 473937
User Picture       phenylethanolamine use & prep

Would Phenyl-1-Hydroxy-2-ethanamine work

That would yield plain amionorex, rather than the desired 4-methylaminorex.

Is benzaldehyde + Nitromethane yielding the Hydroxynitroalkan instead of Nitrostyrene possible?

Yes, using sodium hydroxide as the base and quenching with dropwise addition of dilute acetic acid. It has been discussed before.

BizzyBee
(Stranger)
12-16-03 22:51
No 477257
User Picture       Could 5% acetic acid be used instead of the 2m

Could 5% acetic acid be used instead of the 2m [7%?] hcl?

......../

PoohBearium
(Bear With Me)
12-22-03 01:16
No 478299
      Good work

What a simple reaction, relatively speaking. Is a fume hood a good idea, or just outdoor with a light breeze?

PB

Fuck you, you little _{checken-fucking} chimpanzee!!!

Bandil
(you can always take some more)
12-22-03 11:11
No 478404
      All of the solvents and reactants are quite...

All of the solvents and reactants are quite harmless, so there should be no reason this reaction can't be performed without a fumehood... The only smelly thing that can occur, is if you use to much cyanate, which will result in formed ammonia upon the acidification in the last reaction step.

Regards
Bandil

Drugs = Fun; Drugs <> Money

drjuiceflow
(Stranger)
12-24-03 00:30
No 478737
      One pot synthesis questions/Assistance

Hi Bandil. I was wondering if you could answer the following questions at your earliest convenience?

1. What is the temperature that you set the hot plate for the norephedrine/KOCN reflux?

How about when you add HCL?

How much sodium carbonate do you use to basify ?

Also if I use the exact amount of norephedrine, KOCN, and HCL that you used in the synthesis, will there be ammonia or other smells generated that I should worry about?

Also what brand/type of hotplate and reflux condensers did you use or recommend that someone could purchase for this transaction?

Sorry for all these questions. I will be very grateful if you take the time and answer them.

Rhodium
(Chief Bee)
12-27-03 02:02
No 479195
User Picture       You need to study general organic chemistry

You set the temperature hot enough for the solution to reflux (i.e. boil). That should be 110-120°C for most hotplates.

When adding HCl, the solution should have cooled down to room temp or thereabouts.

You add enough sodium carbonate for the solution to become basic (no precise amount can be given, as this will vary). Check for pH >10 with universal pH paper.

Any hotplate with magnetic stirring will work here, my own favorite being IKAMag (http://www.ika.de/ika/owa/catalog.showBrowse?iProcess=&iGroup=188)

Any reflux condenser will do - UTFSE for "condenser choice"

^{The Hive - Clandestine Chemists Without Borders}

drjuiceflow
(Stranger)
01-03-04 16:28
No 480251
      One more question.......

Should I set up an oilbath and place the reaction flask in the oilbath, or place the reaction flask directly on the hotplate? I would assume oilbath will provide for more even heating of the contents of the flask?

Rhodium
(Chief Bee)
01-03-04 17:31
No 480257
User Picture       Always use baths when refluxing something

I would assume oilbath will provide for more even heating of the contents of the flask?

Yes, that's the main point of using it. Uneven heating may lead to cracking of the glassware and subsequent product loss and/or injury.

^{The Hive - Clandestine Chemists Without Borders}

harry
(Stranger)
02-01-04 04:09
No 485767
      PPA from benzaldehyde and Nitromethane ?

Rhodium said, in answering SS's question on whether "Benz + Nitromethane can produce the hydroxynitoalkan instead of the nitrostyrene" Rhodium said, "Yes, using sodium hydroxide as the base and quenching with dropwise addition of dilute acetic acid. It has been discussed before."

Could some fine bee who knows where this was discussed please point me to its location ? Ive done quite a bit of searching and cannot seem to find this reference. crazy

SWIM has a littre of both benz and nitro just waiting to blossom into PPA. laugh

[blue]edit: Found it ! Tanx anyways. For anyone with the same question the procedure can be found in Psychokitty's post No. 227281

starlight
(Hive Bee)
02-01-04 10:26
No 485817
      i think you have misunderstood

you cannot make PPA using nitromethane. you would need nitroethane otherwise you end up with one too few carbon atoms.

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	All 27 posts		Subject: One pot synthesis of 4-methylaminorex		Please login to post		Down


		Bandil (you can always take some more) 09-12-03 08:23 No 458588				One pot synthesis of 4-methylaminorex (Rated as: excellent)
						Hi! Further exploration of an initial suggestion by Rhodium - to perform both the preparation of the carbamoyl norephedrine as well as its cyclization to trans-4-MAR in one pot gave the following results: Theory: When the initial norephedrine hydrochloride is mixed with potassion cyanate, it forms the carbamoyl coumpound in near quantitatie yeilds with respect to the norephedrine. The original patent's uses a slight molar excess of the cyanate in order to give complete conversion. When the first reaction is done, there should thus be a mixture of: N-carbamoyl-norephedrine, potassiumchloride and traces of of cyanate. The remaining cyanate will be destroyed by the huge excess of acid which will be added later. In the end these impurities should have no influence of the ring formation, catalysed by the acid. It should in theory be possible to do the initial reaction and simply add the acid in one portion while heating continusouly till the reaction is over. With this in mind, it seems kind of a waste to isolate the intermediate, so this has to be tested :) Practice:(in theory of course) 5 grammes of norephedrine.HCl(26,5 mmoles), was placed in a 100 mL FBF, and 2,3 grammes of KOCN(28,4 mmoles) and 25 mL's of distilled water was immediately added in succession. This was heated to reflux directly on the hotplate for two hours. After this time, 30 mL's of 2M HCl(60 mmoles) was added. This caused a bit of bubbling(probably from the excess cyanate being broken down to gasseus -i-cant-remember-what-). Reflux was continued for an additional two hours. The mixture took on an ever so slight pinkish tint, which the "old" synth also tend to do at this stage. After 2½ hours of reflux, the mixture was cooled and basified with sodium carbonate and presto a lot of pretty white crystals precipitated on the bottom of the beaker. The yeild looked like that which is expected from the normal reaction. They will be measured shortly. Conclusion Total success!! We'll the usual cyanate route to 4-methylaminorex was easy, but this is more like baking a shake-n-bake cake really ;)(which is VERY easy if you didn't know). Bioassay's are pending though, but nothing that was put into the flask would have reacted the way, the final product did. The yeild will also be measured shortly! Have a nice and productive weekend! Kind Regards Bandil You can always take some more!



		Megatherium (Hive Bee) 09-12-03 13:35 No 458655				This caused a bit of bubbling(probably from...
						This caused a bit of bubbling(probably from the excess cyanate being broken down to gasseus -i-cant-remember-what-). The isocyanic acid hydrolyzes to NH₃ and CO₂. Congrats, what a beautifull procedure .



		Chimimanie (Hive Bee) 09-14-03 03:40 No 458952				Welldone!
						What a breakthrough! Look so easy! Very very nice! Thank you for the good work (altough were i live E4Euh is illegal ), but still! I cant wait the final yield!



		Rhodium (Chief Bee) 09-16-03 19:25 No 459441				(4-Methyl)Aminorex related forensic article (Rated as: good read)
						Appearance of Aminorex as a Designer Analog of 4-Methylaminorex Marcus E. Brewster and Frank T. Davis Journal of Forensic Sciences 36(2), 587-592 (1991) (https://www.rhodium.ws/chemistry/aminorex.html) Abstract A case in which aminorex (cis (±)-4,5-dihydro-5-phenyl-2-oxazolamine) was prepared as a "designer" analog of a controlled substance, methylaminorex (cis-(±)-4,5-dihydro-4-methyl-5-phenyl-2-oxazolamine) is described. The confiscated drug sample was analyzed by high-field (300-MHz) proton nuclear magnetic resonance (NMR) and carbon-13 NMR spectroscopy, as well as electron impact mass spectrometry (70 eV). These examinations proved conclusively that the material in question was aminorex.



		Bandil (you can always take some more) 09-19-03 17:41 No 459973				Final yield
						The final yield has now been measured: 77% mole wise from the PPA.HCl From 5,0 grammes of PPA.HCl there where prepared 3,6 grammes of 4-methylaminorex freebase with the new method. Compared to the 3,4-dimethylaminorex synthesis from J Chem Soc, 850-854 (1952), it's at least as high as they get, if not higher(i don't have their article lying around, so it's from my clouded memory). This could be attribited to the fact that no collection of the intermediate product is required. All in all, it's not to shabby if i may say so Regards Bandil You can always take some more!



		Rhodium (Chief Bee) 09-19-03 18:36 No 459975				4-MAR mentioned in a blog
						I just wanted to say that I found someones blog with some comments about 4-MAR (http://www.sixthseal.com/000478.html) Same blog, a few days later - Arguments for 4-MAR (http://www.sixthseal.com/000479.html)



		Glacial_Refluxer 10-15-03 00:33				Too bad norephedrine hydrochloride / potassium (Rated as: misinforming)



		Vitus_Verdegast (Hive Bee) 10-15-03 00:42 No 464652				How can you speak for most bees?
						I do agree that norephedrine is harder to obtain, but there is always synthesis (eg. synth the benzaldehyde and nitroethane yourself) and pill extraction for some countries. But for KOCN you are definately talking outta your ass! UTFSE! A Dream Within A Dream (http://www.poedecoder.com/Qrisse/works/dreamw.html)



		Glacial_Refluxer (Hive Bee) 10-16-03 19:54 No 465026				Potassium ferricyanide and potassium ...
						Potassium ferricyanide and potassium thiocyanate are easy to obtain, will they work here? http://www.altavista.com/



		Rhodium (Chief Bee) 10-16-03 21:06 No 465040				UTFSE
						That question has already been asked: Post 455750 (placebo: "If one had a choice between...", Methods Discourse) ...and replied to: Post 455759 (Rhodium: "All three are wrong, unfortunately.", Methods Discourse)



		BottlenecksGhost (Stranger) 10-26-03 12:42 No 466843				Hmm...
						You could be quite mistaken on this one, Rhodium. In the original patent on McNeil Labs 4-methylaminorex Patent GB1021012, page 3, they suggest potassium thiocyanate instead of an alkali cyanate and using this for the ring-closure in an equivalent manner to the normal cyanate-route. In this fascinating little patent, the norephedrine+cyanate+acid method which Bandil, Prometheuz and I thought we had been the first to discover is also suggested.



		Glacial_Refluxer (Hive Bee) 10-28-03 08:19 No 467236				thiocyanate worked
						Swim did not have any luck finding potassium cyanate so he purchased a small amount of potassium thiocyanate, did a small scale rxn assumeing failure. Seeing the rxn take on the pinkish tone surely put a smile on swim's face. Reality?



		SPISSHAK (Hive Addict) 10-30-03 07:12 No 467763				interesting so
						the oxygen on the oxazoline ring could have possibly been substituted by sulfur. Find a guinee pig and try to elucidate the pharmcodynamics of this.



		Nitroxamide (Stranger) 10-30-03 20:19 No 467848				cyanate preparation
						Cyanates are easy to prepare. Simply heat an alkali hydroxide with urea. NaOH + CO(NH2)2 ----> NaOCN + H2O + NH3 Plutonium is a necessary ingredient in the recipe for nirvana.



		Glacial_Refluxer (Hive Bee) 11-28-03 14:55 No 473639				4-MTAR?
						Anyone think that useing the thiocyanate would create something like 4-Methyl-Thio-Amino-Rex? Ive heard of 4-MTA [methyl-thio-amphetamine] a non-nerotoxic seratonin realeaser so.... I wonder if the thio is not a good thing? MTMA hmmmm



		Rhodium (Chief Bee) 11-28-03 16:16 No 473643				That is completely flawed reasoning
						If you look at the structure of 4-Methylthio-Amphetamine and 4-Methylaminorex, you will see that their structures are completely different and that the 4-substituent resides in different parts of their structures.



		SilverSurfer (Hive Bee) 11-30-03 19:08 No 473928				amazing
						Would Phenyl-1-Hydroxy-2-ethanamine work, Is benzaldehyde + Nitromethane yielding the Hydroxynitroalkan instead of Nitrostyrene possible? Could the 1-Hydroxyamine be obtained from reduction of nitrostyrene in any way? Post 404813 (GC_MS: "benzaldehydes + nitromethane pt 1", Methods Discourse) The only purpose of your life may be to serve as a warning to others http://www.despair.com



		Rhodium (Chief Bee) 11-30-03 21:56 No 473937				phenylethanolamine use & prep
						Would Phenyl-1-Hydroxy-2-ethanamine work That would yield plain amionorex, rather than the desired 4-methylaminorex. Is benzaldehyde + Nitromethane yielding the Hydroxynitroalkan instead of Nitrostyrene possible? Yes, using sodium hydroxide as the base and quenching with dropwise addition of dilute acetic acid. It has been discussed before.



		BizzyBee (Stranger) 12-16-03 22:51 No 477257				Could 5% acetic acid be used instead of the 2m
						Could 5% acetic acid be used instead of the 2m [7%?] hcl? ......../



		PoohBearium (Bear With Me) 12-22-03 01:16 No 478299				Good work
						What a simple reaction, relatively speaking. Is a fume hood a good idea, or just outdoor with a light breeze? PB Fuck you, you little _{checken-fucking} chimpanzee!!!



		Bandil (you can always take some more) 12-22-03 11:11 No 478404				All of the solvents and reactants are quite...
						All of the solvents and reactants are quite harmless, so there should be no reason this reaction can't be performed without a fumehood... The only smelly thing that can occur, is if you use to much cyanate, which will result in formed ammonia upon the acidification in the last reaction step. Regards Bandil Drugs = Fun; Drugs <> Money



		drjuiceflow (Stranger) 12-24-03 00:30 No 478737				One pot synthesis questions/Assistance
						Hi Bandil. I was wondering if you could answer the following questions at your earliest convenience? 1. What is the temperature that you set the hot plate for the norephedrine/KOCN reflux? How about when you add HCL? How much sodium carbonate do you use to basify ? Also if I use the exact amount of norephedrine, KOCN, and HCL that you used in the synthesis, will there be ammonia or other smells generated that I should worry about? Also what brand/type of hotplate and reflux condensers did you use or recommend that someone could purchase for this transaction? Sorry for all these questions. I will be very grateful if you take the time and answer them.



		Rhodium (Chief Bee) 12-27-03 02:02 No 479195				You need to study general organic chemistry
						You set the temperature hot enough for the solution to reflux (i.e. boil). That should be 110-120°C for most hotplates. When adding HCl, the solution should have cooled down to room temp or thereabouts. You add enough sodium carbonate for the solution to become basic (no precise amount can be given, as this will vary). Check for pH >10 with universal pH paper. Any hotplate with magnetic stirring will work here, my own favorite being IKAMag (http://www.ika.de/ika/owa/catalog.showBrowse?iProcess=&iGroup=188) Any reflux condenser will do - UTFSE for "condenser choice" ^{The Hive - Clandestine Chemists Without Borders}



		drjuiceflow (Stranger) 01-03-04 16:28 No 480251				One more question.......
						Should I set up an oilbath and place the reaction flask in the oilbath, or place the reaction flask directly on the hotplate? I would assume oilbath will provide for more even heating of the contents of the flask?



		Rhodium (Chief Bee) 01-03-04 17:31 No 480257				Always use baths when refluxing something
						I would assume oilbath will provide for more even heating of the contents of the flask? Yes, that's the main point of using it. Uneven heating may lead to cracking of the glassware and subsequent product loss and/or injury. ^{The Hive - Clandestine Chemists Without Borders}



		harry (Stranger) 02-01-04 04:09 No 485767				PPA from benzaldehyde and Nitromethane ?
						Rhodium said, in answering SS's question on whether "Benz + Nitromethane can produce the hydroxynitoalkan instead of the nitrostyrene" Rhodium said, "Yes, using sodium hydroxide as the base and quenching with dropwise addition of dilute acetic acid. It has been discussed before." Could some fine bee who knows where this was discussed please point me to its location ? Ive done quite a bit of searching and cannot seem to find this reference. SWIM has a littre of both benz and nitro just waiting to blossom into PPA. [blue]edit: Found it ! Tanx anyways. For anyone with the same question the procedure can be found in Psychokitty's post No. 227281



		starlight (Hive Bee) 02-01-04 10:26 No 485817				i think you have misunderstood
						you cannot make PPA using nitromethane. you would need nitroethane otherwise you end up with one too few carbon atoms.

All 27 posts	End of thread	Top