3,4-Methylenedioxybenzyl-(3-azepin-1-yl-propyl)-amine → 3,4-Methylenedioxybenzyl-[3-(3,5-difluorophenyl)-isoxazol-5-yl]-(3-azepin-1-yl-propyl)-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,4-methylenedioxybenzyl-(3-azepin-1-yl-propyl)amine in diethyl ether (26.7 ml of a 0.12 M solution in diethyl ether, 3.22 mmol) cooled to 0° C. is slowly added n-BuLi (1.51 ml of a 1.6M solution in hexane, 2.41 mmol). The resulting mixture is stirred at 0° C. for 10 min and 3-(3,5-difluorophenyl)-5-chloroisoxazole (347 mg, 1.61 mmol) is added at once. After stirring at 0° C. for 30 min, the reaction mixture is dilute with ethyl acetate, washed with water andbrine, dried over sodium sulfate, and concentrated in vacuo. The crude material is purified by flash chromatography (silica gel, 3% methanol containing 10% NH4OH in dichloromethane) to give the free base of the title compound as an oil. The free base is dissolved in dichloromethane (10 ml) and treated with 1 N HCl in diethyl ether (4 ml, 4 mmol) to provide after concentration in vacuo, 3,4-methylenedioxybenzyl-[3-(3,5-difluorophenyl)-isoxazol-5-yl]-(3-azepin-1-yl-propyl)-amine hydrochloride (513 mg, 63%) as a pale yellow foam.

Provenance & Evidence