Water → 4-{3-[4-(3-{4-[amino(propoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-(propoxycarbonyl)benzamidine

Participants

Reaction Steps

Into a solution of 1.71 g of 4-nitrophenyl propyl carbonate in 15 mL of N,N-dimethylformamide, 1.50 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine was added at room temperature, and the solution was stirred at the same temperature for 4 hours. Chloroform and water were added to the reaction mixture. The organic layer was separated, washed with water, twice with a 5% potassium carbonate aqueous solution and with a saturated sodium chloride aqueous solution successively, and dried over anhydrous magnesium sulfate, followed by solvent removal by evaporation under reduced pressure. The obtained residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=4:1). The obtained solid substance was dissolved in chloroform, washed with a 5% potassium carbonate aqueous solution and a saturated sodium chloride aqueous solution successively, and dried over anhydrous magnesium sulfate. After removing the solvent by evaporation under reduced pressure, 1.25 g of 4-{3-[4-(3-{4-[amino(propoxycarbonylimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-(propoxycarbonyl)benzamidine was obtained as a white solid.

Provenance & Evidence