Cyanogen Bromide → 4-Hydroxypiperidine-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A slurry of sodium bicarbonate (24.9 g, 296 mmol) in water (15 mL) was cooled in an ice-bath and a solution of 4-hydroxypiperidine (15 g, 148 mmol) in dichloromethane (25 mL) was added. With rapid stirring, a solution of cyanogen bromide (18.8 g, 177 mmol) in dichloromethane (25 mL) was added dropwise over 15 min. The reaction was stirred for 30 min at ˜4° C., then the cooling bath was removed and the reaction mixture was stirred overnight at room temperature. Sodium carbonate (3 g) and magnesium sulfate (15 g) were added and the mixture was stirred for 30 min, and then filtered. The solids were washed with dichloromethane (50 mL) and the solvents were evaporated from the combined filtrate and washings to give 4-hydroxy-piperidine-1-carbonitrile (15.6 g, 84%) which was used directly in the subsequent step without further purification.

Provenance & Evidence