Ethanol, 2-(cyclohexylamino)- → N-Cyclohexyl-N-(2-hydroxyethyl)-4-[(2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]butanamide

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Reaction Steps

Into 100 ml of chloroform were added 2.5 g of 6-(3-carboxypropoxy)-3,4-dihydrocarbostyril and 1.65 g of 1,8-diazabicyclo[5,4,0]undecene-7. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 1.5 ml of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation, stirring was continued for 30 minutes and 2.0 g of N-(2-hydroxyethyl)cyclohexylamine was added to the reaction mixture and further stirred at a room temperature for 2 hours. After the reaction was completed, the chloroform solution of the reaction product was washed with a diluted NaHCO3 aqueous solution, a diluted hydrochloric acid and water in this order. The chloroform solution was dried with anhydrous Na2SO4, then the chloroform was removed by distillation and the residue thus obtained was recrystallized from chloroform-petroleum ether to obtain 2.1 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. Melting point: 139°-141.5° C.

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