Acetic Acid → HCID 10298483, compound

Participants

Reaction Steps

To a stirred solution of 0.51 g (1.5 mmol) of N-(3-aminophenyl)-2-(4-benzyl-piperidin-1-yl)-oxo-acetamide (Example 11), 0.15 ml (1.5 mmol) of benzaldehyde, 0.18 ml (3 mmol) of acetic acid in 15 ml of dichloroethane 0.48 g (2.25 mmol) of sodium triacetoxyborohydride (Aldrich) is added in small portions below 20° C., and the reaction mixture is stirred at room temperature for 2 hours. Then 30 ml of 8% sodium hydrogencarbonate solution is added to the mixture, the organic layer is separated and the water phase is extracted three times with 30 ml of chloroform. The combined organic layers are dried over sodium sulfate, concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and ethyl acetate:hexane=1:2 as eluent. The product is treated with 2.5 N hydrochloric acid in ethyl acetate solution to yield 0.25 g (36%) of the title compound. Melting Point: 190-207° C. (dec.) (ethyl acetate)

Provenance & Evidence