p-Toluenesulfonic acid monohydrate → HCID 54008509, compound

Participants

Reaction Steps

To a solution of 650 mg (2.1 mmol) of N-(3-benzhydroxypropyl)piperazine in dry tetrahydrofuran (5 ml) was added a solution of 818 mg (2.1 mmol) of N-[5-[3methoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]thiazolidihe-2-thione in dry tetrahydrofuran (6 ml) and the mixture was reacteed at room temperature for 14 hours. The reaction mixture was concentrated by evaporation under reduced pressure and the residue was diluted with chloroform. The mixture was washed, in turn, with 2N aqueous solution of sodium hydroxide and water and the organic layer was dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with 1% methanol in chloroform, to give 1.106 g (1.8 mmol) of N-[5-[3-methoxy-4-(β-methoxyethoxymethoxy)phenyl]-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine. To a solution of 1.064 (2.1 mmol) of the amide compound in methanol (10 ml) was added 370 mg (1.95 mmol) of p-toluenesulfonic acid monohydrate, and the mixture was refluxed for 1.5 hous under argon atmosphere. The mixture was concentrated by evaporation under reduced pressure, diluted with chloroform and washed, in turn, with a saturated aqueous solution of sodium hydrogencarbonate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with a 1 to 2% methanol in chloroform, to give 730 mg (1.42 mmol) of N-[5-(3-methoxy-4-hydroxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine.

Provenance & Evidence