Dicyclohexylcarbodiimide → 1-(3-Methyl-3-phenylbutyl)-4-[2-(3-pyridyl)thiazolidin-4-ylcarbonyl]piperazine

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Reaction Steps

A solution of 2-(3-pyridyl)thiazolidin-4-carboxylic acid (0.81 g), 1-(3-methyl-3-phenylbutyl)-piperazine (0.73 g), 1-hydroxybenzotriazole (0.50 g) and dicyclohexylcarbodiimide (0.76 g) in N,N-dimethylformamide (7 ml) was stirred under room temperature for 12 hours. To the reaction solution was added ethyl acetate (10 ml) and the insoluble matter was filtered off. To the filtrate was added 0.5N sodium hydroxide and the solution was extracted with ethyl acetate. The ethyl acetate layer was extracted with 1N hydrochloric acid. The aqueous layer was made basic with potassium carbonate and extracted with ethyl acetate. The resultant ethyl acetate layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and elution with an ethyl acetate-methanol (10:1) mixture gave 1.32 g of 1-(3-methyl-3-phenylbutyl)-4-[2-(3-pyridyl)thiazolidin-4-ylcarbonyl]piperazine.

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