Hydrochloric Acid → 3-(4-Bromophenyl)-N-methylpropan-1-amine

Participants

Reaction Conditions

Reaction Steps

Borane in THF (1.0 M, 28 mL, 28 mmol) was added dropwise to a solution of 22A (1.6 g, 7.0 mmol) in THF (17.5 mL). After stirring the reaction mixture for 30 min at 0° C. the mixture was refluxed for 4 h. Methanol (20 mL) was added to the mixture at 0° C. followed by the addition of 20 mL 6.0 M HCl dropwise. After refluxing for 30 min the volatiles were removed in vacuo. 50% NaOH (12 mL) was added dropwise while maintaining the temperature below 30° C. The resulting mixture was diluted with water (100 mL) and extracted with diethyl ether (3×100 mL). The organics were combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to yield 22B (1.57 g, 97%) as a clear oil. MS (ESI) m/z 227.99/229.99 (M+H)+.

Provenance & Evidence