Hydrochloric Acid → HCID 178522241, compound

Participants

Reaction Steps

To a solution of 4-(trifluoromethoxy)phenyl isocyanate (2 g, 9.8 mmol) in DMF (100 mL) were added trans-4-aminocyclohexanol hydrochloride (1.6 g, 10.8 mmol) and Et3N (1.5 mL, 10.8 mmol) at 0° C. The reaction mixture was warmed up to room temperature and stirred overnight. After adding aq 1N HCl (20 mL) and water (100 mL), the resulting white precipitates were collected by suction filtration. The collected solid was thoroughly washed with water. Recrystallization from acetone at −78° C. afforded 2.4 g (70%) of the title compound as a white solid. mp 224.1-225.3° C. 1H NMR (300 MHz, DMSO-d6; δ 8.50 (s, 1H), 7.45 (d, J=9 Hz, 2H), 7.21 (d, J=9 Hz, 2H), 6.06 (d, J=8 Hz, 1H), 4.55 (d, J=4 Hz, 1H), 3.44-3.33 (m, 2H), 1.91-1.68 (m, 4H), 1.31-1.07 (m, 4H).

Provenance & Evidence