Ammonia → HCID 19609089, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.2 g (7 mmol) of crude N-bromoacetyl-iminostilbene (38) in 25 mL of chloroform was added carefully to 250 mL of condensed liquid ammonia at -33° C. To the reaction mixture 6.0 g (40 mmol) of sodium iodide was added, the mixture was stirred at -33° C. for 2 hours and evaporated overnight. A water-white oily solution remained and 50 mL of water was added. The solution was extracted with 2×150 mL of chloroform. The solvent was dried over Na2SO4 and evaporated to yield a clear oil that was dissolved in 25 mL of methanol saturated with hydrochloric acid (g). The resulting solution was concentrated and 25 mL of acetonitrile was added. The solid material precipitated was collected and washed with 10 mL of acetonitrile. Recrystallization in methanol/ether gave 1.8 g (6.2 mmol, 90%) of 5-(aminoacetyl)-5H-dibenzo[b,f]azepinehydrochloride (39). NMR, IR and MS data confirmed compound identity.

Provenance & Evidence