Propionyl chloride → Fentanyl

HRID 1948981

Reaktionsgleichung

Reaktionsgleichung von HRID 1948981
[NH:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>ClC(Cl)C>[CH3:24][CH2:23][C:22]([N:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:25]

Komponenten

4

Edukt 2

HCID 62324Propionyl chlorideHCID 88890N-phenyl-1-(2-phenylethyl)-4-piperidinamine

Produkt 1

HCID 3345Fentanyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

In two neck round bottom flask equipped with condenser pressure equalizing funnel and calcium chloride guard tube, a solution of 28.0 (0.10 moles) of 4-anilino N-phenethyl piperidine prepared in step II, in 100 ml of dichloroethane was taken. To this solution, 18.5 gm (0.20 moles) of propionyl chloride was added drop wise through pressure equalizing funnel with continuous stirring. After the completion of the addition, the mixture was further stirred for 1 hrs. After the completion of the reaction, the reaction mixture was washed with 20% sodium hydroxide solution. The aqueous phase was extracted with 2×100 ml of dichloromethane. The combined organic extract was dried over sodium sulphate and concentrated to give crude fentanyl. The crude product was recrystallised from petroleum ether (60 to 80° C.) to give colourless crystals of pure fentanyl having nip 82 to 83° C.

Aufarbeitung

  1. customIn two neck round bottom flask equipped with condenser pressure
  2. additionAfter the completion of the addition
  3. customAfter the completion of the reaction
  4. washthe reaction mixture was washed with 20% sodium hydroxide solution
  5. extractionThe aqueous phase was extracted with 2×100 ml of dichloromethane
  6. extractionThe combined organic extract
  7. dry with materialwas dried over sodium sulphate
  8. concentrationconcentrated
  9. customto give crude fentanyl
  10. customThe crude product was recrystallised from petroleum ether (60 to 80° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f256d7ebde65487ab9a02e5c0fbbd4e3
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399677B2

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