4-chloro-N-cyclohexylbutanamide

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

Procedure: Into 200 ml of dried benzene, 30.6 g of N-γ-chlorobutyrylcyclohexylamine was added. While the inside temperature is kept below 20° C. by ice-cooling the outside of the reaction vessel, 30 g of PCl5 was added under stirring condition. After completion of the addition, the stirring is continued for 2 hours at a room temperature, then the reaction mixture is concentrated to a half volume thereof by using an evaporator with a bath temperature of below 50° C. To the concentrated reaction mixture was added dropwise 140 ml of benzene containing 10% of HN3 under stirring condition for 90 minutes while keeping the inside temperature below 15° C. After the addition operation, the reaction mixture is allowed to stand overnight at room temperature. Then the reaction mixture is refluxed for 3 hours with stirring and is concentrated. The thus obtained concentrate is extracted with 200 ml of chloroform. The chloroform layer is washed with 5% NaHCO3 aqueous solution and with water and dried with Na2SO4. After removal of the drying agent, the mother liquor is concentrated and the residue thus obtained is recrystallized from water-containing isopropanol to obtain 28 g of 1-cyclohexyl-5-γ-chloropropyltetrazole in the form of colorless needle like crystals. Melting point: 82°-85° C. is kept below 20° C. by ice- was added After completion of the addition the reaction mixture is concentrated to a half volume an evaporator with a bath temperature of below 50° C To the concentrated reaction mixture under stirring condition for 90 minutes the inside temperature below 15° C to stand overnight at room temperature Then the reaction mixture is refluxed for 3 hours with stirring is concentrated The thus obtained concentrate is extracted with 200 ml of chloroform The chloroform layer is washed with 5% NaHCO3 aqueous solution and with water dried with Na2SO4 After removal of the drying agent the mother liquor is concentrated the residue thus obtained is recrystallized from water- containing isopropanol

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

Procedure: 0.5 Gram of metallic sodium is dissolved in 50 ml of methanol under ice cooling, and to this solution is added 3.2 g of 6-hydroxy-3,4-dihydrocarbostyril, 3.2 g of sodium iodide and 4.6 g of N-(4-chlorobutyryl)cyclohexylamine, followed by 5-hour refluxing under agitation. After the reaction, the reaction solution is poured into 400 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The resultant crude crystals are recrystallized from methanol to obtain 3.1 g of 6-[3-(N-cyclohexylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 220°-221° C. followed by 5-hour refluxing under agitation After the reaction the precipitated crystals are filtered out washed with water The resultant crude crystals are recrystallized from methanol