Water → HCID 86741625, compound

Participants

Reaction Steps

To a solution of 618 mg (0.929 mmol) of the amide compound in methanol (10 ml) was added 181 (0.952 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 15 hours. 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 chloroform. The organic layer was washed with water and concentrated by evaporation under reduced pressure. The residue was sujected to silica gel column chromatography, eluted with chloroform-methanol (100:1), to give 422 mg (0.766 mmol) of N-[5-(3,5-dimethoxy-4-hydroxyphenyl]-2,4-pentadienoyl]-N'-[2-[1-phenyl-1-(p-chlorophenyl)ethoxy]ethyl]piperazine. Spectrophotometric data of the product support the structure shown below. ##STR126##

Provenance & Evidence