Trifluoroacetic acid → (+/-)-4-(3-Methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt

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To a solution of tert-butyl(+/−)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoate (325 mg, 0.803 mmol) in dichloromethane (8.0 mL) was added trifluoroacetic acid (0.62 mL, 8.0 mmol). The solution was stirred at room temperature for 17 hours then concentrated under reduced pressure. Toluene (3 mL) was added, and the solution was again concentrated under reduced pressure to remove excess trifluoroacetic acid to give (+/−)-4-(3-methyl-1-((3-methylquinolin-2-yl)amino)butyl)benzoic acid trifluoroacetic acid salt as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.26 (s, 1H), 8.06 (d, J=8.4 Hz, 2H), 7.84 (d, J=7.8 Hz, 1H), 7.80-7.75 (m, 1H), 7.75-7.69 (m, 1H), 7.58 (d, J=8.4 Hz, 2H), 7.55-7.48 (m, 1H), 5.50 (dd, J=5.0, 9.5 Hz, 1H), 2.56 (s, 3H), 2.24-2.14 (m, 1H), 1.92-1.75 (m, 2H), 1.08 (d, J=6.4 Hz, 3H), 1.05 (d, J=6.2 Hz, 3H).

Provenance & Evidence