The Vespiary
The Hive => Novel Discourse => Topic started by: ning on May 03, 2004, 08:16:00 PM
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It seems the big problem with the acetaldehyde methylimine grignard reaction is the instability and annoyance of preparing the methylimine. It polymerizes easily, and must be dried rigorously for the grignard to yeild well. How annoying!
What ning proposes is a variation of a well-worn procedure to make PCP--the Bruylants reaction.
I.E. Post 179639 (missing)
(Bwiti: "Help! - 1-Methylaminocyclohexanecarbonitrile", Methods Discourse)
Bwiti made (and unfortunately couldn't use) methylaminocyclohexylcarbonitrile. Now let me ask you this:
What would happen if acetaldehyde, methylamine HCl, and NaCN were reacted? I bet you dollars to donuts the result would bee a fair yield of methylaminoethylcarbonitrile, which could bee based, extracted into nonpolar solvent, dried, and reacted with benzylmagnesium grignard at one's sweet leisure with none of the trouble of the acetaldehyde methylimine route.
Yes, cyanide is poisonous. PCP bees handle it all the time. It can also be made OTC. Ning thinks if this works it might not be such a bad trade, for the convenience and higher yield of a bruylants reaction.
A reaction like this could get PCP bees in the meth market! ;D
Actually, the reason ning likes the grignard method is because it makes SAR exploration so easy! It's like frickin lego blocks here! Any amine + any aldehyde/ketone + any substituted benzyl chloride --> substituted phenethylamine.
With the ease of chloromethylation to produce benzyl chlorides in one step from benzenes, this makes a TERRIFYING number of amphetamine derivatives in reach.
Someone should apply this reaction to MDMA.
catechol --> methylenedioxybenzene --> methylenedioxybenzyl chloride --> MDMA
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Are you sure the grignard reacts in the way you want? Perhaps it just reacts with the nitrile group to make a ketone?
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For one thing, it could only work with dialkylamines, forming a tertiary amine intermediate - else the aminonitrile would have an acidic N-H function left, which would quench the grignard reagent.