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methylating phenethylamine?
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IndoleAmine
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Wed Feb 09, 2005 9:03 am
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Couldn't phenethylamine (obtainable from reductive amination of acetophenone) be methylated with formaldehyde (like in the old Eleusis methylamine FAQ, where ammonium chloride gives methylammonium chloride when reacting with CH2O)?

Acetophenone is cheap, isn't nearly as watched as phenylacetone is, the procedures leading to the amine are essentially the same, and the phenethylamine->amphetamine methylation should be possible with a rxn very similar to a NH4Cl/CH2O reductive methylation.

Any thoughts, comments, critique?
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java
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Wed Feb 09, 2005 11:49 pm
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Although it's true that the methaylation procedure you eluded to by Eleusis did methylate , but it was NH3 that the methyl group was added not to a carbon. I think the procedure may be reserved for that only as I've read where methylation is wanted for the alpha-amino acids, so then decarboxylation can be done and the result would be the amphetamine, and in those suggestions the Eleusis method was never suggested .....as stated because perhaps it will not work on adding a carbon to a chain , other alkylation methods need to be used.......as I read it, java
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java
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Thu Feb 17, 2005 12:44 am
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This is a post from Labrat over at Drug-forum regarding the methylation of the phenethyamines ...........java

----------------------------------------------------------------------------------- Labrat
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Joined: 18 November 2004
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Posts: 37


Posted: 16 February 2005 at 11:40am | IP Logged




Here is one method which can be used to alkylate primary amines at the alpha carbon.


N-benzylate the primary amine to a N-benzylamine. Convert the N-benzylamine to the nitrosoamine. The alpha carbon of the nitrosoamine can be deprotonated by a strong base and thus alkylated with a alkylhalide. Deprotect the alkylated amine. Perhaps I should mention that nitrosoamines are very, very nasty.


Drug-Forum
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