Potassium Iodide → (R,S)-N-Methyl 3-benzylamino-1-phenyl-1-propanol

Participants

Reaction Steps

A solution of 3-chloro-1-phenylpropan-1-ol (2 g, 11.7 mmol), N-methylbenzylamine (2.12 g, 17.5 mmol), potassium iodide (2.6 g, 22 mmol), and potassium carbonate (3.2 g, 23.4 mmol) in dimethylformamide (120 mL) was stirred at 90° C. in a reacti-vial for 16 h. After this time the reaction was allowed to cool to room temperature. The reaction mixture was purified by an SCX-2 column eluting with Methanol followed by ammonia:methanol solution (7 N). The organics were then evaporated and the compound taken directly onto the next step without any further purification. (M+H+1 [256]); δH (300 MHz, CDCl3) 7.2-7.4 (10H, m, Ar), 4.9 (1H, t, CH—OH), 3.55 (1H, d, CH2-Ph), 3.45 (1H, d, CH2—PH), 2.8-3 (1H, m, CH2), 2.55-2.65 (1H, m, CH2), 2.25 (3H, s, CH3), 1.89-1.9 (2H, m, CH2), 1.6 (1H, brs, OH).

Provenance & Evidence