Hydrochloric Acid → HCID 66781309, compound

Participants

Reaction Steps

The mixture of 5-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-2-one (110 mg, 0.45 mmol) in DCE (3 mL) and dimethylamine (2M solution in THF, 5 mL, 4.5 mmol) was treated with sodium triacetoxyborohydride (95 mg, 0.45 mmol) at room temperature. The reaction mixture was stirred for 0.5 h, then the reaction mixture was diluted with saturated NaHCO3, extracted with CH2Cl2(3×), dried over K2CO3, filtered and concentrated in vacuo to afford the target compound. The oily crude residue (96 mg, 79%) was converted to HCl salt. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.11 (t, 1 H) 1.77-1.87 (m, 1 H) 1.96-2.02 (m, 1 H) 2.03-2.22 (m, 3 H) 2.25-2.37 (m, 1 H) 2.81 (d, 3 H) 2.92 (d, 3 H) 3.72-3.90 (m, 1 H) 6.96 (dd, 7 H) 7.21 (d, 7 H) 7.33 (d, 7 H) 12.07-12.30 (broad, 1 H), 13C NMR (126 MHz, CHLOROFORM-d) δ ppm 15.96 (s, 1 C) 24.22 (s, 1 C) 25.84 (s, 1 C) 31.02 (s, 1 C) 33.20 (s, 1 C) 42.65 (s, 1 C) 42.69 (s, 1 C) 69.75 (s, 1 C) 125.96 (s, 1 C) 128.61 (s, 1 C) 130.52 (s, 1 C) 130.57 (s, 1 C) 132.58 (s, 1C) 142.82 (s, 1 C). 13C NMR (400 MHz, CHLOROFORM-d) d ppm 15.96 (s, 1 C) 24.22 (s, 1 C) 25.84 (s, 1 C) 31.02 (s, 1 C) 33.20 (s, 1 C) 42.65 (s, 1 C) 42.69 (s, 1 C) 69.75 (s, 1 C) 125.96 (s, 1 C) 128.61 (s, 1 C) 130.52 (s, 1 C) 130.57 (s, 1 C) 132.58 (s, 1C) 142.82 (s, 1 C). MS (M+1) 270.

Provenance & Evidence