Acetic Acid → HCID 11372753, compound

Participants

Reaction Steps

Mix 4-{5-[(2-Thiophen-2-yl-ethylamino)-methyl]-indol-1-ylmethyl}-benzamide (0.20 g, 0.51 mmol) and acetic acid (5 mL) in a flask. Add sodium cyanoborohydride (0.09 g, 1.52 mmol) and stir for 3 hrs. Neutralize reaction with 5M aqueous NaOH (10 mL) and dilute with water (50 mL). Extract with CH2Cl2 (3×50 mL). Purification on silica using 40:1 CH2Cl2/2M NH3 in CH3OH to 20:1 CH2Cl2/2M NH3 in CH3OH gradient eluent yields the product as an oily substance. Trituration with ether gives the product as a white solid (0.14 g, 72%). Mass spectrum (ion spray): m/z=392.2 (M+1); 1H NMR (DMSO-d6) 7.91 (bs, 1H), 7.82 (d, J=8.1 Hz, 2H), 7.38 (d, J=7.9 Hz, 2H), 7.30 (bs, 1H), 7.27 (d, J=4.8 Hz, 1H), 6.99 (s, 1H), 6.92-6.87 (m, 2H), 6.82 (d, J=2.2 Hz, 1H), 6.46 (d, J=7.9 Hz, 1H), 4.25 (s, 2H), 3.54 (s, 2H), 3.21 (t, J=8.1 Hz, 2H), 2.92-2.81 (m, 4H), 2.69 (t, J=7.1 Hz, 2H).

Provenance & Evidence