Water → HCID 54172614, compound

Participants

Reaction Steps

To a solution of 276 mg (0.456 mmol) of the amide compound in methanol (6 ml) was added 79 mg (0.415 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 20 minutes. Water was added to the reaction mixture, which was adjusted to a pH value of 11 by the addition of an aqueous solution of sodium carbonate and then extracted with ethyl acetate. The organic layer was washed with water and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with chloroform-methanol (20:1), to give 162 mg (0.299 mmol) of 1-[2-[3-(3,5-dimethoxy-4-hydroxyphenyl)-2-propenoyl]aminoethyl]-4-benzhydroxypiperidine.

Provenance & Evidence