Fentanyl → 4-anilino-N-phenethylpiperidone

HRID 1948975

Reaktionsgleichung

CCC([N:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:14][CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=O.C(N1CCCCC1=[O:40])CC1C=CC=CC=1.NC1C=CC=CC=1>>[NH:5]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14](=[O:40])[CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

Edukt 3

HCID 3345Fentanyl

HCID 6115Aniline

HCID 12203238N-phenethylpiperidone

Produkt 1

HCID 104940404-anilino-N-phenethylpiperidoneAusbeute 50 %

Versuchsvorschrift

Fentanyl was first synthesized in 1960 by Paul Janssen founder of Janssen Pharmaceutica involving reacting N-phenethylpiperidone with aniline to produce 4-anilino-N-phenethylpiperidone with yield of about 50-80% using sodium borohydride at room temperature followed by reacting with propionyl chloride in presence of pyridine wherein the reaction is exothermic and thus requires stringent process conditions. The fentanyl thus obtained with a yield over 90% is further purified by crystallization.

Quellen und Nachweise

ORD-Eintrag: ord-75542113e23746eb8562d511a7d26854
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399677B2

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