Example Amine TM

Synthesize the following TM using readily available starting materials and reagents. 

An FGI on the secondary amine TM leads to either an amide or an imine. Further disconnection of either the amide or the imine results in a commercially available electrophile (benzoyl chloride or benzaldehyde, respectively) and an amine nucleophile (2-methylbutan-1-amine). Presumably, this amine structure is complex enough (i.e., expensive enough) that it too should be synthesized, so the retrosynthesis continues with another FGI. The use of an ammonia synthetic equivalent, such as an azide, does not help to simplify the carbon structure, but a retrosynthesis involving a nitrile includes an eventual disconnection of a C-C bond. 

One possible synthesis of the TM begins with the reaction of 2-bromobutane with NaCN. Hydride reduction of the resulting nitrile affords 2-methylbutan-1-amine. Addition of benzoyl chloride and reduction of the resulting amide product installs the second alkyl group on the secondary amine TM. 

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