1-Bromo-2-Chloroethane → 4-Piperidinecarbonitrile, 1-(2-chloroethyl)-

1-Bromo-2-chloroethane (2.6 ml) and potassium carbonate (6.6 g) were added to a solution of 4-cyanopiperidine (2.63 g) in isopropanol (50 ml), followed by refluxing for 10 hours. The reaction mixture was concentrated under reduced pressure. After adding a 50% aqueous solution of potassium carbonate to the residue, the resulting mixture was extracted with diethyl ether. The extract was washed with saturated saline, followed by an addition of anhydrous potassium carbonate to dry the diethyl ether solution. The thus-dried diethyl ether solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (developer: methanol-chloroform) to obtain 0.31 g of the desired product in an oily form.

1. temperatureby refluxing for 10 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionAfter adding a 50% aqueous solution of potassium carbonate to the residue
4. extractionthe resulting mixture was extracted with diethyl ether
5. washThe extract was washed with saturated saline
6. additionfollowed by an addition of anhydrous potassium carbonate
7. dry with materialto dry the diethyl ether solution
8. concentrationThe thus-dried diethyl ether solution was concentrated under reduced pressure
9. customThe residue was purified by silica gel chromatography (developer: methanol-chloroform)

ORD record

ord-01a49f7f7622465398c1f884d08d3fd3

Source dataset

uspto-grants-1988_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04721788