Trifluoroacetic acid → N-{1-[2-(aminomethyl)-4-chlorobenzyl]-2,2,2-trifluoroethyl}-N-(4-methoxyphenyl)amine
Reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:24][CH:25]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:26]([F:29])([F:28])[F:27])=[C:13]([CH:23]=1)[CH2:14][NH:15]C(=O)OC(C)(C)C>C(Cl)Cl>[NH2:15][CH2:14][C:13]1[CH:23]=[C:9]([Cl:8])[CH:10]=[CH:11][C:12]=1[CH2:24][CH:25]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)[C:26]([F:29])([F:28])[F:27]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).