Hydrochloric Acid → HCID 66787649, compound

Participants

Reaction Steps

To a solution 1-[6-(benzothiazol-2-yloxy)-benzofuran-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (342 mg, 0.783 mmol) in IPA (8 mL) was added 2 M KOH (3.9 mL, 7.8 mmol) and stirred (rt, 2 h). The pH of the reaction mixture was adjusted to pH 8 with 1 M HCl (1.7 mL) and partitioned with DCM (30 mL). The aqueous phase was extracted with DCM (3×30 mL). The organic layers were combined, dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC to provide the title compound as a colorless solid (86 mg, 24%). MS (ESI): mass calcd. for C22H20N2O4S, 408.1; m/z found, 408.9 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.78-7.64 (m, 4H), 7.56 (d, J=2.0, 1H), 7.41-7.35 (m, 1H), 7.31-7.27 (m, 1H), 3.90 (5, 2H), 3.61 (5, J=135.2, 1H), 3.17 (d, J=11.3, 3H), 2.36 (t, J=10.9, 3H), 2.11-1.77 (m, 4H).

Provenance & Evidence