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

HRID 232718

反応式

HRID 232718 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-436996e1799b4f9d88fd1db4c47d1188
出典データセット
uspto-grants-1997_01
特許番号
US05591751

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