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

HRID 232718

반응식

HRID 232718 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 233590998-benzylamino-6-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinylcarbonyl}-3,4-dihydrocarbostyril수율 65.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-436996e1799b4f9d88fd1db4c47d1188
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05591751

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