Hydrochloric Acid → 3-[3-(3-Phenylpropyl)-3-azabicyclo[3.1.0]hex-6-yl]phenylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(3-nitrophenyl)-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexan-2-one (Preparation 24, 55 mg, 0.16 mmol) in tetrahydrofuran (3 ml) under nitrogen, was added dropwise at room temperature a 1.0 M solution of lithium aluminium hydride in tetrahydrofuran (0.81 ml, 0.81 mmol). The mixture was heated to 60° C. for 4 h. Further lithium aluminium hydride in tetrahydrofuran (1.0M, 0.3 ml, 0.3 mmol) was added, and the mixture was heated at 60° C. for 20 minutes, then cooled to room temperature. Water (30 ml) was carefully added, then the residue was acidified by the addition of 2N hydrochloric acid (5 ml), and then basified with 2N sodium hydroxide solution (6 ml). The mixture was extracted with ethyl acetate (3×50ml). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was dissolved in ethanol (5 ml), Raney nickel (50 mg) was added, and the mixture was placed under an atmosphere of hydrogen (2 atm, 203 kPa) and stirred at 60° C. for 16 h. The mixture was filtered through Celite™ and concentrated in vacuo to give the title compound as a pale yellow oil (35 mg, 75%).

Provenance & Evidence