1,4-Dibromobutane → Ammonia

Participants

Reaction Steps

A mixture of (±)-3-(3-aminophenyl)-9-methyl-9-azabicyclo[3.3.1]non-2-ene (0.50 g, 2.2 mmol), potassium carbonate (0.61 g, 4.4 mmol), 1.4-dibromobutane (0.52 g, 2.4 mmol) and ethanol (15 ml) was stirred at reflux overnight. The mixture was evaporated and water (25 ml) was added followed by extraction two times with ethyl acetate (25 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as an oil. Yield 0.12 g, 19%.

Provenance & Evidence