Sodium borohydride → HCID 178518613, compound

Participants

Reaction Steps

To a solution of ketone 25 (2.3 g, 9.3 mmol) in 2-propanol (30 mL) was added 4 Å molecular sieves and 3-(4-fluorophenyl)-1-propylamine (1.76 g, 9.3 mmol). The reaction mixture was stirred for 4 hours. Sodium borohydride (0.49 g, 13.03 mmol) was added, and the reaction mixture was stirred overnight, quenched with MeOH, and concentrated under reduced pressure. Purification by flash chromatography (silica, 9.5:5:1 CH2Cl2:MeOH:NH4OH) gave 6-{trans-4-[3-(4-fluorophenyl)propylamino]cyclohexyl}-3H-benzthiazol-2-one (0.24 g, 7%): 1H NMR (500 MHz, DMSO-d6): δ 7.39 (s, 1H), 7.25-7.06 (m, 6H), 3.01 (m, 1H), 2.86 (t, J=8 Hz, 2H), 2.61 (t, J=8 Hz, 2H), 2.37 (m, 1H), 2.01 (m, 2H), 1.92-1.81 (m, 4H), 1.49-1.36 (m, 4H).

Provenance & Evidence