Cyanogen Bromide → 4-Hydroxypiperidine-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

4-Hydroxypiperidine (10 g) is dissolved in 20 ml dichloromethane and added dropwise to a solution of NaHCO3 (16.6 g) in H2O (10 ml) at 0° C. The mixture is stirred at 0° C. for 30 min then 3 M cyanogen bromide (36.3 ml) is added. The mixture is stirred at 0° C. for 30 min then warmed to room temperature for 12 h. The mixture is diluted with dichloroemthane (30 ml) and extracted. The organic layer is washed with brine (15 ml), dried over MgSO4, filtered and concentrated. The crude product is purified by silica gel chromatography (0% to 100% ethyl acetate/hexanes) to afford the title compound. LC (method 20): tR=0.49 min; Mass spectrum (APCI): m/z=127 [M+H]+.

Provenance & Evidence