Trifluoroacetic acid → Trifluoroacetic acid

Participants

Reaction Steps

To a solution of tert-butyl 1-(3,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-3-yl(methyl)carbamate (0.760 g, 1.8 mmol) in dichloromethane (6 mL) was added trifluoroacetic acid (6 mL). The mixture was stirred at room temperature for 1 hour. Solvent was removed under reduced pressure and the residue triturated with hexane and dried under vacuum to give 1-(3,4-dichlorobenzyl)-N-methyl-1,2,3,4-tetrahydroquinolin-3-amine as its solid TFA salt (580 mg). 1H NMR (DMSO) 400 MHz δ 7.57 (m, 2H), 7.28 (dd, J=2.0 Hz and 19.2 Hz, 1H), 7.01 (m, 2H), 6.63 (t, J=7.2 Hz, 1H), 6.54 (d, J=7.6 Hz, 1H), 4.50 (q, J=17.2 Hz, 2H), 3.68 (br, 1H), 3.58 (d, J=12 Hz, 1H), 3.39 (m, 1H), 3.20 (dd, J=5.2 Hz and 16.8 Hz, 1H), 2.89 (dd, J=5.6 Hz, and 16.4 Hz, 1H), 2.63 (t, J=5.2 Hz, 3H). LCMS m/e 321 (M+H).

Provenance & Evidence