Hydrochloric Acid → Benzhydrylamine

Participants

Reaction Steps

A 28% sodium methoxide/methanol solution (0.34 ml; 1.51 molar equivalents) was added to a solution of N-(4-nitrobenzenesulfonyl)benzhydrylamine (402.0 mg) in dry dimethoxyethane (3 ml) at room temperature in a nitrogen atmosphere, followed by stirring for 7 hours at room temperature and for 40 hours under heating at 46 to 49° C. On the way, dry dimethoxyethane (3 ml) was further added after 7 hours, and a 28% sodium methoxide/methanol solution (0.34 ml; 1.51 molar equivalents) was further added about 18 hours after heating. The reaction mixture was cooled with ice, and 1 N hydrochloric acid (5 ml) was added. The reaction solvents were removed by evaporation under reduced pressure, and water (5 ml), 1 N hydrochloric acid (5 ml) and ether (25 ml) were added to the resulting concentrate, followed by extraction and solution separation. The organic layer was extracted again with water (5 ml). Sodium hydroxide (0.61 g) was added to the resulting aqueous layer, and extraction was conducted three times with ether (20 ml), followed by drying over sodium sulfate, filtration, concentration and drying under vacuum to obtain benzhydrylamine (191.2 mg; yield: 95.6%).

Provenance & Evidence