Chloroacetyl chloride → 1-(2-Chloroacetyl)piperidine-4-carbonitrile

Temperature

-10 °C

A mixture of 4-piperidinecarbonitrile (200 g, 1.80 mol) and 40% aqueous potassium carbonate solution (342 g, 0.99 mol) in dichloromethane (1 L) was cooled to −10° C., and a solution of chloroacetyl chloride (210 g, 1.86 mol) in dichloromethane (300 mL) was added over about 75 minutes while maintaining the reaction mixture at −10 to 0° C. After the addition was complete, the reaction mixture was separated, the upper aqueous phase was extracted with dichloromethane (2×300 mL), and the combined organic phases were concentrated under reduced pressure to give 312 g of the title compound as a liquid which slowly crystallized on standing. This compound was of sufficient purity to use in subsequent reactions.

1. temperaturewhile maintaining the reaction mixture at −10 to 0° C
2. additionAfter the addition
3. customthe reaction mixture was separated
4. extractionthe upper aqueous phase was extracted with dichloromethane (2×300 mL)
5. concentrationthe combined organic phases were concentrated under reduced pressure

ORD record

ord-4525a508eb0a41ea8d7f0b2d15459e72

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642634B2