4-(Trifluoromethyl)benzylamine → HCID 67424958, compound

Participants

Reaction Conditions

Reaction Steps

4-trifluoromethylbenzylamine (0.52 ml, 3.6 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (1 g, 3.6 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 25 (400 mg, 2.42 mmol) and TEA (0.34 ml, 1 equiv.) and the mixture was stirred at rt for 8 hours. (TLC AcOEt 1/petroleum ether 1). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 400 mg of a white solid. Yield=45% 1HNMR (DMSO, 200 MHz) δ 4.38 (2H, d, J=6.4 Hz), 4.57 (2H, s), 6.85 (3H, m), 7.59 (2H, d, J=8.2 Hz), 7.72 (2H, d, J=8.4 Hz), 8.15 (1H, bt), 10.61 (1H, bs); [M+1] 367.1 (C17H13F3N2O4 requires 366.3).

Provenance & Evidence