Benzhydrylamine → HCID 58687990, compound

Participants

Reaction Steps

A mixture of the compound from Step H above (1.55 g, 4.26 mmol), aminodiphenylmethane (1.11 mL, 6.40 mmol), and powdered 4 Å molecular sieves (2.80 g) in dichloromethane (20 mL) was stirred for 30 min. Then sodium triacetoxyborohydride (132 mg, 0.625 mmol) was added. The resultant mixture was stirred overnight, diluted with dichloromethane, filtered, and the filtrate was washed with saturated aqueous sodium carbonate solution. The layers were separated, and the aqueous solution was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure, and the residue was purified by flash chromatography (silica gel; dichloromethane as eluant) to yield the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.48 (s, 1H), 7.18-7.38 (m, 10H), 4.84 (s, 1H), 4.78 (s, 2H), 3.81 (s, 3H), 2.77 (m, 4H), 1.62 (br s, 1H), 0.97 (s, 9H), 0.12 (s, 6H). LC/MS: 531 (M+1).

Provenance & Evidence