Hydrochloric Acid → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 151 g of 4-phenylpiperidine-4-carboxylic acid p-toluenesulfonate and 213 g of aqueous 30% NaOH solution in 500 ml of water is cooled to 5° C. A solution of 68.2 g of benzyl chloroformate in 150 ml of acetone is added dropwise and the mixture is stirred for 6 days while allowing the temperature to return to rt. 150 ml of acetone are added and the reaction mixture is poured onto a mixture of 200 g of concentrated HCl solution, 300 ml of water and 300 ml of acetone precooled on an ice bath. The precipitate formed is filtered off by suction and washed with water and then with ether. 89.7 g of the expected product are obtained.

Provenance & Evidence