4-(Trifluoromethyl)benzylamine → HCID 53476469, compound

Participants

Reaction Conditions

Reaction Steps

Commercially available 4-trifluoromethylbenzylamine (0.6 ml, 4.2 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (1.2 g, 4.2 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 1f (460 mg, 2.8 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt). 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 250 mg of a white solid. Yield=24% 1HNMR (DMSO, 200 MHz) δ 4.31 (2H, d, J=6.2 Hz), 6.46 (1H, dd), 6.70 (2H, t), 6.81 (1H, t), 7.45 (2H, d, J=8 Hz), 7.70 (4H, m), 8.16 (1H, s), 10.72 (1H, bs); [M+1] 366.1 (C17H14F3N3O3 requires 365.3).

Provenance & Evidence