Toluene → 3-(4-Methoxy-phenoxy)-propylamine

Participants

Reaction Steps

Under an argon atmosphere, 3-(4-methoxyphenoxy)propionitrile (5.0 g) was dissolved in tetrahydrofuran (20 mL), and borane-tetrahydrofuran complex (1.02 mol/L, 30.0 mL) was added dropwise at 80° C. for 10 minutes. After stirring for 3 hours at the same temperature, the reaction liquor was returned to room temperature. In an ice-cold bath, a 4 N aqueous sodium hydroxide solution (30 mL) was added for 10 minutes. After 10 minutes, the mixture was stirred at room temperature for 5 minutes, and then stirred at 80° C. for 12 hours. The mixture was returned to room temperature, and toluene (100 mL) was added, and the mixture was stirred for 1 hour, and then insoluble material was removed using Celite. An organic layer was isolated, and washed with water (100 mL×2 times) and saturated brine (100 mL), and then dried over anhydrous sodium sulfate (80 g). The resultant was filtered, and then the filtrate was concentrated under reduced pressure to obtain a white solid (4.0 g, 79.0%).

Provenance & Evidence