Hydrochloric Acid → HCID 19379084, compound

Participants

Reaction Steps

To a stirred solution of 2-[4-(3-cyclopentylidenemethyl-4-methoxy-phenyl)-piperidin-1-yl]-oxo-acetic acid ethyl ester (0.4 mmol, 0.150 g) in methanol (5 mL) was added hydroxylamine.HCl (1.6 mmol, 0.111 g), followed by potassium hydroxide/methanol solution (5 M solution; 0.4 mL) dropwise at room temperature. A white solid precipitated out of solution as this reaction stirred for 3 hours. The reaction went to completion as seen by TLC. The reaction mixture was diluted with H2O (100 mL), acidified with 1N HCl and extracted with EtOAc (3×100 mL). Each organic phase was washed with H2O (1×50 mL) and the combined organics were dried (Na2SO4) and concentrated in vacuo to a white solid. The solid was triturated in Et2O/hexane to afford pure white crystals which were dried overnight at 45° C. to give the title compound, mp 127°-128° C. (0.3 mmol, 0.017 g, 75%).

Provenance & Evidence