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All 15 posts Subject: Phenylacetaldehyde + MeNH2 (g) in methanol Please login to post Down

tropine
(Newbee)
11-12-03 02:03
No 470334
      Phenylacetaldehyde + MeNH2 (g) in methanol

a 250 gram bottle of phenylacetaldehyde (50% in isopropol alcohol) is mixed with the equivalent amount of MeNH2 dissolved in methanol @ 0 C. The solvent is then removed in rotovap to dryness. This is then immediately dissolved in ether and and the equivalent amount of MeMgBr is added. Any comments?

Aurelius
(Active Asperger Archivist)
11-12-03 05:07
No 470380
      Grignard and Imine?

Is this what your are proposing to yield amphetamine?

Act quickly or not at all.

tropine
(Newbee)
11-12-03 16:01
No 470485
      yes, I am also wondering if instead of MeMgBr,

actually I think it would yield methampethamine, I am also wondering if instead of MeMgBr, one could use MeLi

Aurelius
(Active Asperger Archivist)
11-13-03 06:19
No 470607
      addition

The second equivalent might add to the nitrogen, but if it does actually do so, I see no reason that it won't dimethylate. It would probably be best to use one eq. to yield amphetamine and then mono-methylate using procedures found here and at Rhodium's.

Act quickly or not at all.

josef_k
(Hive Bee)
11-13-03 15:37
No 470663
      The methyl gringard does not add to the ...

The methyl gringard does not add to the nitrogen, but to the carbon in the imine doublebond. This is what he's going to do: https://www.rhodium.ws/chemistry/meth.phenylacetaldehyde.html

tropine
(Newbee)
11-13-03 15:41
No 470664
      exactly, but..

yes that is what I am refering to, but I am wondering if MeLi can be substituted for the grignard, and what kind of conditions are used for MeLi, as in room temp or -78?

Aurelius
(Active Asperger Archivist)
11-14-03 04:42
No 470783
      Temp and Lithium

Yes, the Li comp will also work, and -78*C probably isn't necessary, but it should probably be kept well below 0*C.

(embarrassing, josef_k is absolutely right about the addition- I understood the addition to the imine, but didn't realize the rest- it should have been obvious )

Act quickly or not at all.

josef_k
(Hive Bee)
11-15-03 15:52
No 471044
      While you're at it you should try to use ...

While you're at it you should try to use EtMgBr too, to get 1-phenyl-2-methylaminobutane. I don't think anyone here has made it yet?

Vitus_Verdegast
(Hive Addict)
11-15-03 16:28
No 471050
User Picture       1-phenyl-2-(methyl)aminobutane

SWIM is busy at the moment wink

Reports to follow soon...

Flight of the Bumble Bee (http://www.geocities.com/eric_vornoff/BumbleBee.mp3)

Aurelius
(Active Asperger Archivist)
11-15-03 20:36
No 471095
      Methyl analog

Yes, somebody has already made it. Although it was not me, I have tried it. Decent stimulant, though weak. good for a little bit of a mood lift and energy boost- much like caffiene, but stronger.

I've tried on several occassions to contact the person who had made it, but He/She has been gone without notice for the longest time.

Act quickly or not at all.

moo
(Hive Bee)
11-15-03 20:54
No 471099
      Maybe it should be called aephetamine, as in a

Maybe it should be called aephetamine, as in alpha-ethylphenethylamine. smile

If one was looking for a practical stimulant lacking the side-effects of caffeine while being milder and shorter lasting than plain amphetamine, could this be it?

_{fear fear hate hate}

Aurelius
(Active Asperger Archivist)
11-17-03 07:06
No 471324
      Tastings

Depends on which side effects you are talking about. Caffience doesn't have a lot of side effects (at least not many serious, commonly encountered side effects). From experience, it leaves a good taste in the nose.

Act quickly or not at all.

Vitus_Verdegast
(Hive Addict)
11-17-03 13:59
No 471367
User Picture       aephetamine

Hehe, nice name, but the compound is already named butanamine in post Post 461403 (Chimimanie: "Ariadne and the Butanamines", Serious Chemistry)

We could use both names of course..

Flight of the Bumble Bee (http://www.geocities.com/eric_vornoff/BumbleBee.mp3)

roger2003
(Hive Bee)
11-17-03 14:54
No 471375
      1-phenyl-2-pyrrolidylbutane

I think, this would be the best

wink

roger2003

Kinetic
(Hive Bee)
11-19-03 21:24
No 471815
      2-methylamino-1-phenylbutane
(Rated as: good read)

Aurelius, to the best of my knowledge, nobody knows exactly what's happened to the bee you mention. Fingers crossed he's safe...

2-methylamino-1-phenylbutane is a pet project of mine, mainly because of it's legal status, but also because it's a cheap way to test new methods before wasting more valuable precursors.

I made it from the corresponding ephedrine analogue (which was made from benzene -> butyrophenone -> methcathinone analogue), but after a crappy workup put me in a really bad mood, I threw away the 6g impure salt which refused to precipitate after titration of the freebase... Hence I'm yet to bioassay it.

tropine: I'd be cautious if you're planning on using methyllithium instead of the weaker methylmagnesium halide, as it may well work as an efficient base, deprotonating the benzylic carbon of the phenylacetaldehyde methylimine. I've tried a Grignard with ethylmagnesium iodide on the similar benzyl cyanide, only to be left with a strange smelling orange goo, which I suspect is formed by deprotonation of the benzylic carbon of benzyl cyanide, and subsequent attack by this on another molecule of benzyl cyanide. The end result is a trimer: 6-benzyl-3,5-diphenyl-pyridine-2,4-diyldiamine (courtesy of Beilstein). I'm not sure how much of a problem this will be with the N-methyl imine instead of the nitrile; deprotonation would still be favourable, going on the stability of primary vs. benzylic carbanions. This may not be a problem of course: Rhodium has a very respectable yield of amphetamine in his One Pot Amphetamine synth from BzCN, MeI and NaBH4 (https://www.rhodium.ws/chemistry/amphetamine.html); low temperature and high dilution (hence slow addition) favour the desired reaction.

I'm intrigued about 1-phenyl-2-pyrrolidinylbutane; very similar in structure to Prolintane. wink Do you have any more details, roger? Specifically on effects, as the synthesis would be really easy, either from phenyl-2-butanone, or via reduction of the cathinone analogue 1-phenyl-2-(1-pyrrolidinyl)-1-butanone...

Vitus, I'm not sure if you'll beat me to 2-methylamino-1-phenylbutane or not; I'll post details too, whenever I get there. From one method, I have some 1,2-epoxide which I'll hopefully be able to rearrange to phenyl-2-butanone (LiI was unsuccessful); whether that works or not, triethylaluminium on benzyl cyanide should do the job, as per a slight modification of P2P by Trimethylaluminium alkylation of Benzyl cyanide (https://www.rhodium.ws/chemistry/phenylacetone.html#me3al), a method which seems to initially come from Aust. J. Chem, 23, (1970), 1921-1937, in which trimethylaluminium is reacted with 4-fluorobenzyl cyanide to give 4-fluorophenylacetone.

I'll post any relevant details once I retrieve the article.

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	All 15 posts		Subject: Phenylacetaldehyde + MeNH2 (g) in methanol		Please login to post		Down


		tropine (Newbee) 11-12-03 02:03 No 470334				Phenylacetaldehyde + MeNH2 (g) in methanol
						a 250 gram bottle of phenylacetaldehyde (50% in isopropol alcohol) is mixed with the equivalent amount of MeNH2 dissolved in methanol @ 0 C. The solvent is then removed in rotovap to dryness. This is then immediately dissolved in ether and and the equivalent amount of MeMgBr is added. Any comments?



		Aurelius (Active Asperger Archivist) 11-12-03 05:07 No 470380				Grignard and Imine?
						Is this what your are proposing to yield amphetamine? Act quickly or not at all.



		tropine (Newbee) 11-12-03 16:01 No 470485				yes, I am also wondering if instead of MeMgBr,
						actually I think it would yield methampethamine, I am also wondering if instead of MeMgBr, one could use MeLi



		Aurelius (Active Asperger Archivist) 11-13-03 06:19 No 470607				addition
						The second equivalent might add to the nitrogen, but if it does actually do so, I see no reason that it won't dimethylate. It would probably be best to use one eq. to yield amphetamine and then mono-methylate using procedures found here and at Rhodium's. Act quickly or not at all.



		josef_k (Hive Bee) 11-13-03 15:37 No 470663				The methyl gringard does not add to the ...
						The methyl gringard does not add to the nitrogen, but to the carbon in the imine doublebond. This is what he's going to do: https://www.rhodium.ws/chemistry/meth.phenylacetaldehyde.html



		tropine (Newbee) 11-13-03 15:41 No 470664				exactly, but..
						yes that is what I am refering to, but I am wondering if MeLi can be substituted for the grignard, and what kind of conditions are used for MeLi, as in room temp or -78?



		Aurelius (Active Asperger Archivist) 11-14-03 04:42 No 470783				Temp and Lithium
						Yes, the Li comp will also work, and -78C probably isn't necessary, but it should probably be kept well below 0C. (embarrassing, josef_k is absolutely right about the addition- I understood the addition to the imine, but didn't realize the rest- it should have been obvious ) Act quickly or not at all.



		josef_k (Hive Bee) 11-15-03 15:52 No 471044				While you're at it you should try to use ...
						While you're at it you should try to use EtMgBr too, to get 1-phenyl-2-methylaminobutane. I don't think anyone here has made it yet?



		Vitus_Verdegast (Hive Addict) 11-15-03 16:28 No 471050				1-phenyl-2-(methyl)aminobutane
						SWIM is busy at the moment Reports to follow soon... Flight of the Bumble Bee (http://www.geocities.com/eric_vornoff/BumbleBee.mp3)



		Aurelius (Active Asperger Archivist) 11-15-03 20:36 No 471095				Methyl analog
						Yes, somebody has already made it. Although it was not me, I have tried it. Decent stimulant, though weak. good for a little bit of a mood lift and energy boost- much like caffiene, but stronger. I've tried on several occassions to contact the person who had made it, but He/She has been gone without notice for the longest time. Act quickly or not at all.



		moo (Hive Bee) 11-15-03 20:54 No 471099				Maybe it should be called aephetamine, as in a
						Maybe it should be called aephetamine, as in alpha-ethylphenethylamine. If one was looking for a practical stimulant lacking the side-effects of caffeine while being milder and shorter lasting than plain amphetamine, could this be it? _{fear fear hate hate}



		Aurelius (Active Asperger Archivist) 11-17-03 07:06 No 471324				Tastings
						Depends on which side effects you are talking about. Caffience doesn't have a lot of side effects (at least not many serious, commonly encountered side effects). From experience, it leaves a good taste in the nose. Act quickly or not at all.



		Vitus_Verdegast (Hive Addict) 11-17-03 13:59 No 471367				aephetamine
						Hehe, nice name, but the compound is already named butanamine in post Post 461403 (Chimimanie: "Ariadne and the Butanamines", Serious Chemistry) We could use both names of course.. Flight of the Bumble Bee (http://www.geocities.com/eric_vornoff/BumbleBee.mp3)



		roger2003 (Hive Bee) 11-17-03 14:54 No 471375				1-phenyl-2-pyrrolidylbutane
						I think, this would be the best roger2003



		Kinetic (Hive Bee) 11-19-03 21:24 No 471815				2-methylamino-1-phenylbutane (Rated as: good read)
						Aurelius, to the best of my knowledge, nobody knows exactly what's happened to the bee you mention. Fingers crossed he's safe... 2-methylamino-1-phenylbutane is a pet project of mine, mainly because of it's legal status, but also because it's a cheap way to test new methods before wasting more valuable precursors. I made it from the corresponding ephedrine analogue (which was made from benzene -> butyrophenone -> methcathinone analogue), but after a crappy workup put me in a really bad mood, I threw away the 6g impure salt which refused to precipitate after titration of the freebase... Hence I'm yet to bioassay it. tropine: I'd be cautious if you're planning on using methyllithium instead of the weaker methylmagnesium halide, as it may well work as an efficient base, deprotonating the benzylic carbon of the phenylacetaldehyde methylimine. I've tried a Grignard with ethylmagnesium iodide on the similar benzyl cyanide, only to be left with a strange smelling orange goo, which I suspect is formed by deprotonation of the benzylic carbon of benzyl cyanide, and subsequent attack by this on another molecule of benzyl cyanide. The end result is a trimer: 6-benzyl-3,5-diphenyl-pyridine-2,4-diyldiamine (courtesy of Beilstein). I'm not sure how much of a problem this will be with the N-methyl imine instead of the nitrile; deprotonation would still be favourable, going on the stability of primary vs. benzylic carbanions. This may not be a problem of course: Rhodium has a very respectable yield of amphetamine in his One Pot Amphetamine synth from BzCN, MeI and NaBH4 (https://www.rhodium.ws/chemistry/amphetamine.html); low temperature and high dilution (hence slow addition) favour the desired reaction. I'm intrigued about 1-phenyl-2-pyrrolidinylbutane; very similar in structure to Prolintane. Do you have any more details, roger? Specifically on effects, as the synthesis would be really easy, either from phenyl-2-butanone, or via reduction of the cathinone analogue 1-phenyl-2-(1-pyrrolidinyl)-1-butanone... Vitus, I'm not sure if you'll beat me to 2-methylamino-1-phenylbutane or not; I'll post details too, whenever I get there. From one method, I have some 1,2-epoxide which I'll hopefully be able to rearrange to phenyl-2-butanone (LiI was unsuccessful); whether that works or not, triethylaluminium on benzyl cyanide should do the job, as per a slight modification of P2P by Trimethylaluminium alkylation of Benzyl cyanide (https://www.rhodium.ws/chemistry/phenylacetone.html#me3al), a method which seems to initially come from Aust. J. Chem, 23, (1970), 1921-1937, in which trimethylaluminium is reacted with 4-fluorobenzyl cyanide to give 4-fluorophenylacetone. I'll post any relevant details once I retrieve the article.

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