Reaktion #319900

Reaktionsgleichung

benzaldehyde

8-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril

sodium boron hydride

→

8-benzylamino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril

Ausbeute 65.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed
2. 2
   Temperaturby heating, for 4 hours in an oil bath
3. 3
   Temperaturto cool
4. 4
   workup.DISTILLATIONsubjected to distillation under reduced pressure
5. 5
   Sonstigeto remove the solvent
6. 6
   workup.ADDITIONThe residue was mixed with water
7. 7
   ExtraktionThe mixture was extracted with methylene chloride
8. 8
   TrocknenThe extract was dried with anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONsubjected to distillation
10. 10
    Sonstigeto remove the solvent
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (elutant: methylene chloride/methanol=100/1~50/1~20/1)
12. 12
    workup.DISTILLATIONThe eluate was subjected to distillation
13. 13
    Sonstigeto remove the solvent
14. 14
    SonstigeThe residue was recrystallized from ethanol-n-hexane

Vorschrift

In 10 ml of ethanol was dissolved 1 g of 8-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril. Thereto was added 0.3 g of benzaldehyde. The mixture was refluxed by heating, for 4 hours in an oil bath. The reaction mixture was allowed to cool and then mixed with 0.15 g of sodium boron hydride. The mixture was stirred at room temperature for 4 hours and subjected to distillation under reduced pressure to remove the solvent. The residue was mixed with water. The mixture was extracted with methylene chloride. The extract was dried with anhydrous sodium sulfate and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: methylene chloride/methanol=100/1~50/1~20/1). The eluate was subjected to distillation to remove the solvent. The residue was recrystallized from ethanol-n-hexane to obtain 0.8 g of 8-benzylamino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril as a light yellow powder having a melting point of 144.5°-145.5° C.

Quelle