Water → HCID 127950, compound

Participants

Reaction Steps

To a solution of 690 mg (1.15 mmol) of the amide compound in methanol (14 ml) was added 212 mg (1.12 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 25 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 (50:1), to give 393 mg (0.730 mmol) of 1-[2-[5-(3-methoxy-4-hydroxyphenyl)-2,4-pentadienoyl]aminoethyl]4-benzhydroxypiperidine.

Provenance & Evidence