Synthesis of Amines via Reduction Reactions

The C N triple bond of nitriles can be reduced with LiAlHi or by catalytic hydrogenation to give amine products. Since the cyano group can be introduced via an Sn2 on an alkyl halide, this offers a useful route to amine TMs. 

Note that the cyanide nucleophile introduces both nitrogen and a new carbon. This extra carbon must be accounted for in the retrosynthetic planning. 

Amine Synthesis via Amides (RCOjH - RCONHR RCHaNHRO 

Reduction of amides with LiAlHi adds two equivalents of hydride to afford amine products. Reaction of an acid chloride with an amine (ammonia NH3, primary RNH2, or secondary R2NH) generates the desired amide product. 

A possible retrosynthesis of an amine TM begins with an FGI to an amide by inserting a carbonyl on one of the alkyl groups. Disconnection of the amide at the C-N bond leads to the required add chloride and amino starting materials. 

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