Benzhydrylamine → HCID 178420361, compound

Participants

Reaction Steps

To a solution of 4-phenylcyclohexanone (500 mg, 2.87 mmol) and diphenylmethanamine (526 mg, 2.87 mmol) in DCE (4 mL) at 0° C. was added sodium triacetoxyborohydride (912 mg, 4.30 mmol) by portions slowly. A white suspension resulted and was stirred for 5 min before the ice-water bath was removed. The reaction was stirred at rt for 1.5 h. The reaction was quenched with water carefully, then saturated NaHCO3 was added carefully and the aqueous was extracted with DCM (3×). The organic layers were combined, washed with brine, dried over Na2SO4, and concentrated. The residue was purified by ISCO flash chromatography (0-100% hexane/EtOAc) to give Intermediate 30A (734 mg, 2.149 mmol, 74.9% yield) and trans-N-benzhydryl-4-phenylcyclohexanamine (191 mg, 0.559 mmol, 19.49% yield), LC-MS (ESI) m/z 342.1 (M+H), RT=1.76 min (Method B). 1H NMR (400 MHz, chloroform-d) δ ppm 7.37 (4 H, d, J=7.33 Hz), 7.23-7.31 (6 H, m), 7.11-7.23 (5 H, m), 4.91 (1 H, s), 2.80-2.88 (1 H, m), 2.46-2.56 (1 H, m), 1.74-1.90 (4 H, m), 1.60-1.70 (2H, m), 1.47-1.59 (2 H, m).

Provenance & Evidence