Hydrochloric Acid → HCID 49833165, compound

Participants

Reaction Steps

To a solution of 1-{2-[5-(benzothiazol-2-yloxy)-1H-indol-3-yl]-ethyl}-piperidine-4-carboxylic acid ethyl ester (44 mg, 0.098 mmol) in isopropanol (2.5 mL) was added H2O (1.1 mL) followed by KOH (11 mg, 0.19 mmol) in H2O (2.5 mL) and the resulting reaction mixture was stirred (rt, 16 h). The reaction mixture was acidified with 6 N HCl to pH 6 and treated with DCM (10 mL). The layers were separated and the aqueous layer was extracted with 25% isopropanol/DCM (2×10 mL). The combined organic layers were dried, filtered and concentrated in vacuo to afford the title compound as a white solid (43 mg, 100%). MS (ESI): mass calcd. for, C23H23N3O3S, 421.5; m/z found, 422.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.76 (d, J=8.0, 1H), 7.66 (m, 2H), 7.51 (d, J=8.7, 1H), 7.43 (m, 1H), 7.36 (s, 1H), 7.31 (m, 1H), 7.16 (dd, J=8.7, 2.3, 1H), 5.20 (s, 2H), 3.94 (m, 1H), 3.30-3.14 (m, 2H), 2.54-2.30 (m, 1H), 2.23-2.04 (m, 2H), 1.30 (s, 2H), 1.17 (d, J=6.2, 4H).

Provenance & Evidence