Triethylamine → HCID 178518610, compound

Participants

Reaction Steps

To a solution of 3-(4-Chlorophenyl)-1-propylamine hydrochloride (1.5 g, 7.3 mmol) in 2-propanol (50 mL) was added Et3N (1.1 mL, 8.0 mmol), ketone 5 (1.7 g, 7.3 mmol), THF (25 mL), and 3 Å molecular sieves. The reaction mixture was warmed to dissolve ketone 5 and then stirred at room temperature for 2.25 hours. Sodium borohydride (550 mg, 14.5 mmol) was added, and the reaction mixture was stirred for 12 hours. The reaction was quenched with MeOH, and the mixture was filtered through a pad of Celite and concentrated under reduced pressure. Purification by flash chromatography (silica, 90:10 CH2Cl2/MeOH) followed by trituration/recrystallization with MeOH gave 6-{trans-4-[3-(4-chlorophenyl)propylamino]cyclohexyl}-3H-benzoxazol-2-one (683 mg, 24%), as a white solid: 1H NMR (500 MHz, DMSO-d6): δ 7.32 (d, J=8 Hz, 2H), 7.23 (d, J=8 Hz, 2H), 7.12 (s, 1H), 6.98-6.93 (m, 2H), 2.61 (t, J=7 Hz, 2H), 2.56 (t, J=7 Hz, 2H), 2.48-2.38 (m, 2H), 1.94 (br d, J=10 Hz, 2H), 1.77 (br d, J=10 Hz, 2H), 1.72-1.66 (m, 2H), 1.44 (dddd, J=12, 12, 12, 3 Hz, 2H), 1.12 (dddd, J=12, 12, 12, 3 Hz, 2H).

Provenance & Evidence