4-(Trifluoromethoxy)benzylamine → HCID 67479167, compound

Participants

Reaction Steps

To a solution of 3.3 (491 mg, 1.280 mmol) and TEA (535 μL, 3.84 mmol) in DCM (6402 μL) was added HATU (536 mg, 1.409 mmol) followed by 4-(trifluoromethoxy)benzylamine (Apollo Scientific Ltd., 215 μL 1.409 mmol) The reaction was stirred at room temperature for 40 hours. The reaction then was concentrated and the residue was adsorbed onto a plug of silica gel and purified by chromatography through a 50 g silica gel column, eluting with 0.5 to 5% MeOH in DCM, to provide 3 as a light purple solid in 23% yield. 1H NMR (300 MHz, CD3OD) δ ppm 1.62 (br. s., 1H) 1.79-1.93 (m, 2H) 1.93-2.10 (m, 1H) 2.54 (br. s., 1H) 3.12 (br. s., 4H) 3.35-3.52 (m, 2H) 3.81 (br. s., 4H) 4.22-4.37 (m, 4H) 6.45 (d, J=7.31 Hz, 1H) 6.99 (d, J=8.62 Hz, 2H) 7.21 (d, J=8.04 Hz, 2H) 7.33 (t, J=8.40 Hz, 4H) 7.65 (d, J=7.31 Hz, 1H); M+H 557.24764.

Provenance & Evidence