Hydrochloric Acid → HCID 19379079, compound

Participants

Reaction Steps

To a stirred solution of 2-[4-(3-cycloheptylidenemethyl-4-methoxy-phenyl)-piperidin-1-yl]-oxo-acetic acid ethyl ester (0.6 mmol, 0.250 g) in methanol (5 mL) was added hydroxylamine.HCl (2.4 mmol, 0.167 g, followed by KOH/MeOH solution (5M, 600 μL) dropwise at room temperature. A white solid precipitated out of solution at this reaction continued to stir overnight at room temperature. The reaction went to completion as seen by TLC. The reaction mixture was diluted with H2O (150 mL), acidified with 1N HCl and then extracted with EtOAc (3×100 mL). Each organic phase was washed with H2O (1×100 mL) and the combined organics were dried (Na2SO4) and concentrated to yield a white solid. The solid was triturated in Et2O/hexane to afford the pure title compound, mp 135°-136° C. (0.3 mmol, 0.125 g, 54%).

Provenance & Evidence