N-(3-benzhydroxypropyl)piperazine → N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine

Participants

Reaction Steps

To a solution of 310 mg (1 mmol) of N-(3-benzhydroxypropyl)piperazine in dry tetrahydrofuran (5 ml) was added a solution of 483 mg (1 mmol) of N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]thiazolidine-2-thione in dry tetrahydrofuran (5 ml), and the mixture was allowed to react at room temperature for overnight under argon atmosphere. The reaction mixture was concentrated by evaporation under reduced pressure, diluted with chloroform and washed; in turn, with 2N aqueous solution of sodium hydroxide 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 chloroform-methanol (50:1), to give 470 mg (0.89 mmol) of N-[5-(3,4-dimethoxyphenyl)-2,4-pentadienoyl]-N'-(3-benzhydroxypropyl)piperazine. Spectrophotometric data of the product support the structure shown below. ##STR107##

Provenance & Evidence