Potassium Carbonate → {1-[2-(4-Fluorophenyl)ethyl]-piperidin-3-ylmethyl}carbamic Acid Benzyl Ester

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Reaction Steps

A solution of 3-(benzyloxycarbonylaminomethyl)-piperidine hydrochloride (199 mg, 690 μmol) was dissolved in aqueous sodium hydrogen carbonate and the solution was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was combined with toluene-4-sulfonic acid 2-(4-fluorophenyl)ethyl ester (97 mg, 690 μmol) and potassium carbonate (190 mg, 1.38 mmol) in acetone (15 mL) and the mixture was heated at reflux for 17 hours. The mixture was cooled, diluted with water, and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash chromatography, eluting with ethyl acetate, to provide a white solid (140 mg, 66%). 1H NMR (300 MHz, CD3OD) δ7.30 (m, 5H), 7.22 (m, 2H), 6.99 (t, J=9 Hz, 2H), 5.07 (s, 2H), 3.1-2.7 (m, 5H), 2.55 (m, 2H), 2.00 (m, 1H), 1.8-1.5 (m, 4H), 0.98 (m, 1H). Mass spec (ES+) m/z 371.4 (M+H+, 100%).

Provenance & Evidence