Diethyl Ether → Demethylfentanyl

HRID 1973792노트

반응식

HRID 1973792 반응식
IC.[O:3]([CH2:6][CH3:7])CC.[Li].[C:9]1([NH:15][C:16]2(C(O)=O)[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[C:9]1([NH:15][C:16]2([C:6](=[O:3])[CH3:7])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18][CH2:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 3283Diethyl Ether3회HCID 6328Methyl iodideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 3028194Lithium

생성물 1

HCID 191586Demethylfentanyl

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To start the reaction, a small amount of a solution of 78.1 parts of iodomethane in 70 parts of dry 1,1'-oxybisethane is dropped to a stirred solution of 6.9 parts of lithium in 70 parts of dry 1,1'-oxybisethane. After the addition of 70 parts of dry 1,1'-oxybisethane, the remainder of the solution is added dropwise at reflux temperature. Stirring at reflux is continued for 30 minutes. Then there were added portionwise 16.2 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid (a violent reaction occurs whereby reflux temperature is maintained). Upon completion, stirring at reflux is continued for 1h. 30. The reaction mixture is decomposed by the dropwise addition of 300 parts of water. The organic phase is separated, washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The first fraction is collected and the eluent is evaporated. The residue is crystallized from 14 parts of 2,2'-oxybispropane, yielding 1-[4-(phenylamino)-1-(2-phenylethyl)-4-piperidinyl]ethanone; mp. 100.6° C.

후처리

  1. customthe reaction
  2. additionthe remainder of the solution is added dropwise
  3. temperatureat reflux temperature
  4. temperatureat reflux
  5. customa violent reaction
  6. temperaturereflux temperature
  7. temperatureis maintained)
  8. stirringUpon completion, stirring
  9. temperatureat reflux
  10. waitis continued for 1h
  11. customThe organic phase is separated
  12. washwashed with water
  13. customdried
  14. filtrationfiltered
  15. customevaporated
  16. customThe residue is purified by column-chromatography over silica gel using
  17. additiona mixture of trichloromethane and 5% of methanol as eluent
  18. customThe first fraction is collected
  19. customthe eluent is evaporated
  20. customThe residue is crystallized from 14 parts of 2,2'-oxybispropane

출처 및 근거

ORD 기록
ord-9c1de255318641aab594c1fa29d8fbd8
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03998834

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