Réaction #319900

Équation de réaction

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

Rendement 65.5%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was refluxed
2. 2
   Températureby heating, for 4 hours in an oil bath
3. 3
   Températureto cool
4. 4
   workup.DISTILLATIONsubjected to distillation under reduced pressure
5. 5
   Autreto remove the solvent
6. 6
   workup.ADDITIONThe residue was mixed with water
7. 7
   ExtractionThe mixture was extracted with methylene chloride
8. 8
   SéchageThe extract was dried with anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONsubjected to distillation
10. 10
    Autreto remove the solvent
11. 11
    AutreThe 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
    Autreto remove the solvent
14. 14
    AutreThe residue was recrystallized from ethanol-n-hexane

Mode opératoire

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.

Source