Ammonium Chloride → Tert-butyl 4-(2H-tetrazol-5-YL)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 4-cyanopiperidine-1-carboxylate (2.1 g), sodium azide (1.95 g) and ammonium chloride (1.6 g) in dimethylformamide was heated to 100° C. for 18 hours. The mixture was cooled and partitioned between 1N HCl and dichloromethane. The organic layer was washed with water, dried (MgSO4) and evaporated to give a gum which was purified by column chromatography eluting with MeOH/dichloromethane (1:99) to give tert-butyl 4-(2H-tetrazol-5-yl)piperidine-1-carboxylate (1.31 g); NMR (CDCl3): 1.5 (s, 9H), 1.9 (m, 2H), 2.15 (m, 2H), 3.0 (m, 2H), 3.3 (m, 1H), 4.2 (m, 2H).

Provenance & Evidence