Sodium Cyanide → 4-Cyanomethyl-1-diphenylmethylpiperidine

Participants

Reaction Conditions

Reaction Steps

Step 3): NaCN (2.5 g, 51 mmol) was added to a solution of 1-diphenylmethyl-4-chloromethyl-piperidine (8.9 g, 29.7 mmol) in dimethyl sulfoxide (DMSO) (100 ml). The mixture was heated at 60° C. for 20 hours and then poured into 3% NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (10% ethyl acetate in hexane) to give 4-cyanomethyl-1-diphenylmethylpiperidine (61.4%): mp 103°-104° C. and 3-(2-cyanoethyl)-1-diphenylmethyl pyrrolidine (20.9%):oil.

Provenance & Evidence