Water → HCID 19919567, compound

Participants

Reaction Steps

To partially dissolved 1-[4-(4-phenethyl-piperazin-1-yl)benzo[b]thiophen-2-yl]-ethanone hydrochloride (0.92 g, 2.5 mmol, product from Example 42) in methanol (70 mL) is added sodium borohydride (0.19 g, 5.0 mmol). After 0.33 h, the reaction is clear and homogeneous. The reaction is worked up after 2 h by pouring into water (10 mL), extracting with dichloromethane (3×75 mL), and concentrating the sodium sulfate dried extracts in vacuo. The product (Rf of 0.3 in ethyl acetate) is dissolved in acetonitrile (50 mL), treated with 1.0M hydrochloric acid (2.5 mL), concentrated in vacuo, then reconcentrated from acetonitrile:methanol to give a white solid. After vacuum drying for 9 h at 70° C., the title compound is isolated as a white solid (0.865 g). 1H NMR (d6 -DMSO): 11.48 (1H, bs), 7.61 (1H, d, J=8.0 Hz), 7.40-7.23 (7H), 6.95 (1H, d, J=7.6 Hz), 5.76 (1H, bs), 5.07 (1H, q, J=6.2 Hz), 3.69 (2H, bd, J=10.6 Hz), 3.53 (2H, m), 3.45-3.25(6H), 3.17 (2H, m), 1.50 (3H, d, J=6.4 Hz) ppm. 13C NMR (d6 -DMSO): 152.13, 146.05, 139.74, 137.10, 133.35, 128.67, 126.79, 124.47, 117.62, 116.20, 112.54, 64.86, 56.19, 51.18, 48.45, 48.24, 29.29, 25.68 ppm. IR (KBr): 3351, 2575, 2554, 2446, 1570 cm-1. CIMS (methane): 367 (92%), 349 (100%), 275 (82% ).

Provenance & Evidence