Hydrochloric Acid → HCID 59577602, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[6-(benzothiazol-2-yloxy)-1H-indol-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (410 mg, 0.094 mmol) in isopropanol (10 mL) was added aqueous KOH (2 M, 53 mg, 0.42 mL, 0.94 mmol) and the resulting solution was heated (90° C., 24 h). The reaction mixture was diluted with H2O (10 mL) and neutralized with aqueous 1 M HCl. The suspension was filtered and the solid was washed with EtOAc (20 mL) and dried in vacuo to provide the title compound as a tan solid (128 mg, 33%). MS (ESI): mass calcd. for C22H21N3O3S, 407.4; m/z found, 408.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 11.18 (5, 1H), 7.88 (d, J=9.7, 1H), 7.73 (d, J=10.8, 1H), 7.68 (d, J=10.0, 1H), 7.44-7.40 (m, 2H), 7.35-7.28 (m, 2H), 7.06-7.03 (m, 1H), 3.66 (5, 2H), 2.88-2.84 (m, 2H), 2.22-2.16 (m, 1H), 2.04-2.00 (m, 2H), 1.80-1.77 (m, 2H), 1.58-1.55 (m, 2H), the CO2H proton was not detected.

Provenance & Evidence