Hydrochloric Acid → 4-Cycloheptyloxy-benzylamine

Participants

Reaction Conditions

Reaction Steps

Dissolve 4-cycloheptyloxy-benzonitrile (2 g, 9.29 mmol) in anhydrous THF (20 mL) and cool to 0° C. Add borane dimethylsulfide complex (2.8 mL, 27.9 mmol, 10-12 M solution), stir at 0° C. for 0.5 h and then heat at reflux for 1 h. Cool the mixture to 0° C., add methanol (5 mL) and stir for 15 min. Add 2M aqueous HCl (15 mL) and stir for 30 min at room temperature. Concentrate the mixture in vacuo and purify the residue by chromatography on silica gel (45 g RediSep column) eluting with a gradient of dichloromethane in chloroform/methanol/concentrated ammonium hydroxide (80:18:2) over 30 min (80 ml/min) to provide the title compound as a colorless oil (1.87 g, 97%). MS (APCI) m/z: 220 (M+H)+.

Provenance & Evidence