Nitrogen mustard hydrochloride → HCID 20344006, compound

Participants

Reaction Steps

2.3 g of 99% sodium hydride are slowly added to a mixture, under nitrogen, of 4.3 g of 2-(4-fluorophenylthio)-benzyl cyanide in 30 mls of dimethylsulfoxide. After total addition, the mixture is stirred for an additional five minutes and then a mixture of 3.9 g of 95% mechlorethamine hydrochloride in 20 ml of dimethylsulfoxide is added portionwise over a 40 minute span. After this addition, the reaction is stirred for 1 hour in a hot water bath at 70° C. and then permitted to stand at ambient temperature for 16 hours. The cooled reaction mixture is poured onto 150 ml of crushed ice and the diluted mixture is extracted thrice with 60 ml portions of ether. The combined ether extracts are washed with 25 ml of saturated sodium chloride solution and dried, leaving a solid. The solid is recrystallized from cyclohexane, leaving the pure product, 4-cyano-4-[2-(4-fluorophenylthio)phenyl]-1-methylpiperidine.

Provenance & Evidence