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All 6 posts Subject: phenethylamines from benzoic acids ? Please login to post Down

xxxxx
(Stranger)
04-24-04 22:13
No 502739
      phenethylamines from benzoic acids ?

a benzoic acid ester is condensed with NaOEt and diethyl malonate to form c6h5coch(cooet)2. a mannich reaction is performed with coh2 and nh3 to form c6h5coc(ch2nh2)(cooet)2.
sometimes a carbon monoxide moiety can be expelled by heating if it is adjacent to electron withdrawing groups such as cooet. would like to ask if this would occur with this compound and what temperature (160C?) would be required and yield. if carbonyl moiety is expelled then heating with sulfuric acid would remove cooet groups leaving phenethylamine.

Nicodem
(Hive Bee)
04-25-04 08:59
No 502813
User Picture       Learn to count carbons?

You can't remove that carbonyl by heathing (this is not like -CO-COOH!). Only the ester groups can bee hydrolised and decarboxylated simultaneously at 90 - 100°C in aq. acid. And you can't make that Mannich bases with ammonia. Only dialkylamines give useful yield, ammonia gives a trialkylated Mannich base.

“The real drug-problem is that we need more and better drugs.” – J. Ott

xxxxx
(Stranger)
04-26-04 16:27
No 503138
      utility of alpha-keto ethyl benzene

would the compound c6h5coch3 result from the heating with acid? this might have some synthetic utulity.

Rhodium
(Chief Bee)
04-27-04 00:05
No 503215
User Picture       malonic synthesis of acetophenone

Yes. That compound is called acetophenone, and its preparation via the acylation of diethyl malonate is described in the article linked in Post 503140 (Rhodium: "P2P by acylation of diethyl malonate", Methods Discourse)

^{The Hive - Clandestine Chemists Without Borders}

xxxxx
(Stranger)
05-03-04 16:56
No 504600
      proposed process

1) ethyl benzoate condensed with ethyl acetate to form c6h5coch2cooc2h5. 2) reduce ketone to c6h5ch2ch2cooc2h5. 3)add ammonia in alcohol to form c6h5ch2ch2conh2. 4) react with hypochlorite to form c6h5ch2ch2nh2. would this process work or not? which steps might be most difficult/low yielding?

ning
(acetaminophanatic)
05-03-04 23:32
No 504642
User Picture       Could you write more clearly?

And get beilstein or something.

1. This step should have a reference. Yields vary. Seems doable, but. Hm. You'd need a strong base, like NaOEt, unless the PTC Claisen condensation pans out.
Why not use acetonitrile instead? It already has the amine present.

2. Wolff-kishner or Clemmenson reduction. Got hydrazine?

3. Try using urea instead. UTFSE for Eleusis's methylamine FAQ, where they perform such an operation to make acetamide.

4. Hoffmann rearrangement. Doable. Yields ning has seen are in the ~50% region, depending very much on how activated the ring is to halogenation, one of the competing reactions.

Dude, format your posts better if you want people to read them!

The major advantage of your proposed scheme is that (if it works) it offers a route to substituted cathinones or their phenethylamine equivalents. (i.e. don't remove the ketone part)

Barring that, I imagine most bees who could rustle up the hydrazine and sodium ethoxide required for your idea could find some nitromethane and aluminum foil instead. Ah, well.

I've been chased by both cops and robbers. So what does that make me?

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	All 6 posts		Subject: phenethylamines from benzoic acids ?		Please login to post		Down


		xxxxx (Stranger) 04-24-04 22:13 No 502739				phenethylamines from benzoic acids ?
						a benzoic acid ester is condensed with NaOEt and diethyl malonate to form c6h5coch(cooet)2. a mannich reaction is performed with coh2 and nh3 to form c6h5coc(ch2nh2)(cooet)2. sometimes a carbon monoxide moiety can be expelled by heating if it is adjacent to electron withdrawing groups such as cooet. would like to ask if this would occur with this compound and what temperature (160C?) would be required and yield. if carbonyl moiety is expelled then heating with sulfuric acid would remove cooet groups leaving phenethylamine.



		Nicodem (Hive Bee) 04-25-04 08:59 No 502813				Learn to count carbons?
						You can't remove that carbonyl by heathing (this is not like -CO-COOH!). Only the ester groups can bee hydrolised and decarboxylated simultaneously at 90 - 100°C in aq. acid. And you can't make that Mannich bases with ammonia. Only dialkylamines give useful yield, ammonia gives a trialkylated Mannich base. “The real drug-problem is that we need more and better drugs.” – J. Ott



		xxxxx (Stranger) 04-26-04 16:27 No 503138				utility of alpha-keto ethyl benzene
						would the compound c6h5coch3 result from the heating with acid? this might have some synthetic utulity.



		Rhodium (Chief Bee) 04-27-04 00:05 No 503215				malonic synthesis of acetophenone
						Yes. That compound is called acetophenone, and its preparation via the acylation of diethyl malonate is described in the article linked in Post 503140 (Rhodium: "P2P by acylation of diethyl malonate", Methods Discourse) ^{The Hive - Clandestine Chemists Without Borders}



		xxxxx (Stranger) 05-03-04 16:56 No 504600				proposed process
						1) ethyl benzoate condensed with ethyl acetate to form c6h5coch2cooc2h5. 2) reduce ketone to c6h5ch2ch2cooc2h5. 3)add ammonia in alcohol to form c6h5ch2ch2conh2. 4) react with hypochlorite to form c6h5ch2ch2nh2. would this process work or not? which steps might be most difficult/low yielding?



		ning (acetaminophanatic) 05-03-04 23:32 No 504642				Could you write more clearly?
						And get beilstein or something. 1. This step should have a reference. Yields vary. Seems doable, but. Hm. You'd need a strong base, like NaOEt, unless the PTC Claisen condensation pans out. Why not use acetonitrile instead? It already has the amine present. 2. Wolff-kishner or Clemmenson reduction. Got hydrazine? 3. Try using urea instead. UTFSE for Eleusis's methylamine FAQ, where they perform such an operation to make acetamide. 4. Hoffmann rearrangement. Doable. Yields ning has seen are in the ~50% region, depending very much on how activated the ring is to halogenation, one of the competing reactions. Dude, format your posts better if you want people to read them! The major advantage of your proposed scheme is that (if it works) it offers a route to substituted cathinones or their phenethylamine equivalents. (i.e. don't remove the ketone part) Barring that, I imagine most bees who could rustle up the hydrazine and sodium ethoxide required for your idea could find some nitromethane and aluminum foil instead. Ah, well. I've been chased by both cops and robbers. So what does that make me?

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