Hydrochloric Acid → HCID 59662178, compound

Participants

Reaction Conditions

Reaction Steps

2-{1-[2-(3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethyl]-piperidin-4-yl}-benzoic acid methyl ester Compound 93 (1.2 g, 3.0 mmol) was dissolved in THF (10 mL) and treated with lithium hydroxide monohydrate (864 mg, 21 mmol). The reaction mixture was heated to 40° C. for 24 hrs, cooled to rt, adjusted to pH 3 with 1N HCl, and concentrated in vacuo. Purification by Gilson HPLC (elution with 10 to 90 gradient of H2O 0.2% TFA buffer/acetonitrile with 0.1% TFA buffer) afforded Compound 3-1 as a white solid (1.45 g, 2.93 mmol, 98%). 1H NMR (300 MHz, CDCl3) δ 8.71 (d, J=5 Hz, 1H), 7.92 (m, 1H), 7.59-7.43 (m, 2H), 7.32-7.22 (m, 1H), 7.14-6.89 (m, 3H), 4.62 (s, 2H), 3.97-3.68 (m, 2H), 3.45-2.94 (m, 4H), 2.71-2.33 (m, 3H), 2.13-1.96 (m, 2H), 1.80-1.65 (m, 2H); MS (ES+) m/z 381.1 (M+1).

Provenance & Evidence