Sodium Cyanide → 4-Amino-4-cyano-1-phenyl-piperidine

Participants

Reaction Steps

N-Phenyl-4-piperidone (2.3 g, 13 mmol, 1.0 equiv) was dissolved in 26 mL of 2 M NH3 in MeOH and NaCN (0.76 g, 15 mmol, 1.2 equiv) and NH4Cl (0.80 g, 15 mmol, 1.2 equiv) were added and the mixture was refluxed for 2 h at which time an additional 26 mL of 2 M NH3/MeOH was added followed by another 2 h of reflux. The reaction mixture was cooled and filtered. The filtrate was concentrated. The crude product was purified by flash chromatography on SiO2 eluting with 100% CH2Cl2 and 2% MeOH in CH2Cl2 to give the pure product (1.92 g) as a thick yellow oil which solidified on standing; MS, m/z 202=M+1.

Provenance & Evidence