Acrylonitrile → 3-[(1-benzyl-4-piperidyl)oxy]propanenitrile

Participants

Reaction Steps

Sodium hydride [50% w/w in mineral oil] (2.0 g) was added to a slurry of 1-benzyl-4-piperidinol (400 g) and acrylonitrile (530 g) at 0° C. over 1 hour. The reaction mixture was warmed slowly to room temperature and stirred for 18 hours after which time the acrylonitrile was removed under reduced pressure and the residue taken up in isopropanol (1 L). The resulting yellow precipitate was filtered off. The filtrate was evaporated under reduced pressure to afford an orange oil which was dissolved in dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by distillation to afford 2-[(1-benzyl-4-piperidyl)oxy]ethyl cyanide (308 g), b.p. 150-160° C. @ 0.2 mmHg.

Provenance & Evidence