Pyridine → 6-(4-Chlorophenyl)-1-phenyl-2-piperidone

Participants

Reaction Steps

(2)-(a) A solution of 17.8 g of 5-anilino-5-(4-chlorophenyl)pentanoic acid in a mixed solution of 290 ml of toluene and 13.9 g of pyridine was cooled to -3° C. and stirred. To this solution was added 10 ml solution of 5.1 ml of thionyl chloride in toluene dropwise over 1 hour. After stirring at -3° C. for 1 hour and at room temperature for 1.5 hours, the reaction mixture was poured into ice-water. The toluene layer was washed with diluted hydrochloric acid, a saturated aqueous sodium chloride solution, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried and treated with activated charcoal. After removal of charcoal and the solvent, the residual solid was recrystallized from isopropyl ether to give 16.4 g of 6-(4-chlorophenyl)-1-phenyl-2-piperidone as colorless prisms.

Provenance & Evidence