Cyanogen Bromide → 4-Hydroxypiperidine-1-carbonitrile

Temperature

0 °C

4-Hydroxypiperidine (10 g) dissolved in dichloromethane (20 ml) is 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 and then 3 M cyanogen bromide (36.3 ml) is added. The mixture is stirred at 0° C. for 30 min and then at room temperature for 12 h. The mixture is extracted with dichloromethane. The combined organic layer is washed with brine (15 ml), dried (MgSO4), filtered and concentrated. The crude product is purified by chromatography on silica gel (ethyl acetate/hexane 0:1→1:0) to afford the title compound.

1. stirringThe mixture is stirred at 0° C. for 30 min
2. waitat room temperature for 12 h
3. extractionThe mixture is extracted with dichloromethane
4. washThe combined organic layer is washed with brine (15 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product is purified by chromatography on silica gel (ethyl acetate/hexane 0:1→1:0)

ORD record

ord-d3b597ebc89a44efab6fc30b6a2ac5ec

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822471B2