Ammonium Chloride → Hydrochloric Acid

Participants

Reaction Steps

A mixture of 5.16 g of 3-(4-cyanobutyl)-N-(3-pyridyl)indole, 1.88 g of sodium azide, 1.57 g of ammonium chloride and 10 mole % of lithium chloride is heated in 14 ml of dry N,N-dimethylformamide at 125° C. for 17 hours. The reaction mixture is cooled, filtered and evaporated to a residual oil which is partitioned between 50 ml of water and 50 ml of ethyl acetate. The aqueous phase is adjusted to pH=2, extracted with 20 ml of ethyl acetate, adjusted to pH=5 and the resulting solid collected by filtration. Treatment with 6.2 ml of 3N ethereal hydrogen chloride yields 3-[4-(5-tetrazolyl)butyl]-N-(3-pyridyl)indole hydrochloride.

Provenance & Evidence