Potassium Carbonate → HCID 14873777, compound

Participants

Reaction Steps

A mixture of 4-[(1-oxopropyl)phenylamino]-piperidine (500 mg, 2.15 mmol), prepared according to the procedure of P. A. J. Janssen et al, U.S. Pat. No. 3,164,600, methyl bromoacetate (0.25 ml, 2.58 mmol), and potassium carbonate (594 mg, 4.3 mmol), in acetonitrile (2.5 ml) is stirred at room temperature for five hours. The reaction mixture is diluted with 1:1 water and ethyl acetate (20 ml total). The phases are separated and the aqueous phase extracted with ethyl acetate (2×) and the combined organics washed with brine, dried over sodium sulfate and then concentrated. The residue is chromatographed on silica gel (95/5 CHCl3 /MeOH) to give 4-[(1-oxopropyl)phenylamino]-1-piperidineacetic acid, methyl ester, as an oil: 348 mg, 53% yield. An equimolar amount of maleic acid in ether is added to a solution of the free base in ethyl acetate to give the maleate salt as a white solid; maleate salt: m.p. 130°-133° C.

Provenance & Evidence