Pyridine → 4-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride

Participants

Reaction Steps

A mixture of 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (1 g, 4.3 mmol), pyridine (680 mg, 8.6 mmol), and triphosgene (430 mg, 1.45 mmol) in toluene (20 ml) was heated under reflux for 3 hours. The reaction mixture was allowed to return to room temperature and diluted with diethyl ether. The mixture was washed with 10% hydrochloric acid, water and brine in this order, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure to afford 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride (1 g, yield 90%) as a yellow oil.

Provenance & Evidence