Propionyl chloride → Fentanyl

HRID 1948983

반응식

HRID 1948983 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 3345Fentanyl

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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 150 ml of dichloroethane was taken. To this solution, 9.25 gm (0.10 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 10 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 mp 82 to 83° C.

후처리

  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.)

출처 및 근거

ORD 기록
ord-f66d9b4e924b4dcf8db083810bc19569
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399677B2

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