Acrylonitrile → 1-(3-Aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine

Participants

Reaction Steps

As an alternative to obtaining a mixture of Schiff bases VI and VI(a) or VI(b), the reaction can be conducted stepwise. For example, 4-(2-aminoethyl)piperidine may be converted to a Schiff base with 1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]pentan-3-one, catalytically reduced, the ring nitrogen selectively cyanoethylated with acrylonitrile, followed by catalytic hydrogenation to furnish 1-(3-aminopropyl)-4-[2-(1,5-di-[3,3-dimethylbicyclo[2.2.1]hept-2-yl]-3-pentylamino)ethyl]piperidine.

Provenance & Evidence