3-(cyclohexylmethylamino)propan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into 400 ml of chloroform, were added 5 g of 6-(4-carboxybutoxy)-3,4-dihydrocarbostyril and 3.2 g of DBU. The outside of the reaction vessel containing the above mentioned mixture was ice-cooled and 2.8 g of isobutyl chloroformate was added dropwise to the mixture under stirring condition. After the addition operation, stirring was continued at a room temperature for 30 minutes and 3.9 g of N-(3-hydroxypropyl)-N-cyclohexylmethylamine was added to the reaction mixture and the reaction was continued for 3 hours. After the reaction was completed, the reaction mixture was washed with 1 N-NaOH aqueous solution, 10% HCl and water in this order and was dried with anhydrous Na2SO4. The drying agent was removed by filtration and the thus obtained dried product was concentrated to obtain a residue. The residue was treated by a silica-gel column chromatography (solvent used was a mixture of chloroform:methanol=40:1). The elute obtained was concentrated and was recrystallized from ethyl acetate-petroleum ether. 4.0 Grams of 6-{4-[N-cyclohexylmethyl-N-(3-hydroxypropyl)aminocarbonyl]butoxy}-3,4-dihydrocarbostyril was obtained in the form of colorless needle-like crystals. Melting point: 95°-97° C. The outside of the reaction vessel containing the cooled After the addition operation, stirring the reaction was continued for 3 hours the reaction mixture was washed with 1 N-NaOH aqueous solution, 10% HCl and water in this order was dried with anhydrous Na2SO4 The drying agent was removed by filtration the thus obtained dried product was concentrated to obtain a residue The residue was treated by a silica-gel column chromatography (solvent The elute obtained was concentrated was recrystallized from ethyl acetate-petroleum ether