Trifluoroacetic acid → N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine

Participants

Reaction Steps

TFA (1 mL) was added to a stirred solution of tert-butyl 5-chloro-2-{2-[(4-methoxyphenyl)amino]-3,3,3-trifluoropropyl}benzylcarbamate (0.205 g, 0.447 mmol) in CH2Cl2 (2 mL). After 1 h the solvent was evaporated in vacuo and the residue was partitioned between EtOAc and saturated aqueous Na2CO3. The organic layer was dried (Na2SO4) and evaporated in vacuo to give N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine (0.182 a solid; 1H NMR (CDCl3, 400 MHz) δ 3.02 (dd, J=10.9 and 14.2 Hz, 1H), 3.11 (dd, J=3.4 and 14.2 Hz, 1H), 3.69 (s, 3H), 3.86 (d, J=12.9 Hz, 1H), 3.97 (d, J=12.9 Hz, 1H), 3.98 (obscured m, 1H), 6.44 (d, J=8.8 Hz, 2H), 6.66 (d, J=8.8 Hz, 2H), 7.19 (s, 2H), 7.22 (s, 1H).

Provenance & Evidence