Diethyl Ether → Demethylfentanyl

HRID 1448290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1448290
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

Komponenten

6

Edukt 4

HCID 3283Diethyl Ether3×HCID 6328Methyl iodideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 3028194Lithium

Produkt 1

HCID 191586Demethylfentanyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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 are 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 1 h. 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 silicagel 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.

Aufarbeitung

  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 1 h
  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 silicagel
  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

Quellen und Nachweise

ORD-Eintrag
ord-3d4b8e8e5ad14346a2c2270f0a37fde0
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04179569

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