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

HRID 232718

Reaktionsgleichung

Reaktionsgleichung von HRID 232718
[NH2:1][C:2]1[CH:3]=[C:4]([C:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:30])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:17][CH2:16]2)=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.B.[Na]>C(O)C>[CH2:31]([NH:1][C:2]1[CH:3]=[C:4]([C:13]([N:15]2[CH2:20][CH2:19][CH:18]([N:21]([CH3:30])[CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:17][CH2:16]2)=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 233590718-amino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyrilHCID 178418435HCID 178418435, Verbindung

Produkt 1

HCID 233590998-benzylamino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyrilAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. temperatureby heating, for 4 hours in an oil bath
  3. temperatureto cool
  4. distillationsubjected to distillation under reduced pressure
  5. customto remove the solvent
  6. additionThe residue was mixed with water
  7. extractionThe mixture was extracted with methylene chloride
  8. dry with materialThe extract was dried with anhydrous sodium sulfate
  9. distillationsubjected to distillation
  10. customto remove the solvent
  11. customThe residue was purified by silica gel column chromatography (elutant: methylene chloride/methanol=100/1~50/1~20/1)
  12. distillationThe eluate was subjected to distillation
  13. customto remove the solvent
  14. customThe residue was recrystallized from ethanol-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-436996e1799b4f9d88fd1db4c47d1188
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591751

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