Hydrochloric Acid → 1-Benzyl-4-(dimethylamino)piperidine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

208 g (3 equiv.) of N,N-dimethylamine hydrochloride, 154 g (3 equiv.) of potassium cyanide in 154 ml of water and 1050 ml (7 equiv.) of a 40% aqueous dimethylamine solution were added to a solution of 150 g (1 equiv.) of 1-benzyl-piperidin-4-one in 300 ml of methanol, and the mixture was cooled to 0° C. 75 ml (0.5 equiv.) of concentrated hydrochloric acid were then added at 0° C. and the reaction mixture was stirred for 24 hours at room temperature. The progress of the reaction was monitored by thin-layer chromatography (20% EtOAc/hexane). When the reaction was complete, the solid that had formed was filtered off and washed with ice-water (4 l). The resulting solid was then dissolved in ethyl acetate and dried with Na2SO4. After removal of the solvent under reduced pressure, 165 g (85%) of crude product were obtained in the form of a solid.

Provenance & Evidence