Cyanogen Bromide → 4-Hydroxypiperidine-1-carbonitrile

Temperature

0 °C

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]+.

1. stirringThe mixture is stirred at 0° C. for 30 min
2. temperaturethen warmed to room temperature for 12 h
3. additionThe mixture is diluted with dichloroemthane (30 ml)
4. extractionextracted
5. washThe organic layer is washed with brine (15 ml)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude product is purified by silica gel chromatography (0% to 100% ethyl acetate/hexanes)

ORD record

ord-174cc352173349d0af317e9d70320734

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921398B2