Fentanyl → 4-anilino-N-phenethylpiperidone

HRID 1948975

Reaction equation

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

Participants

Reactant 3

HCID 3345Fentanyl

HCID 6115Aniline

HCID 12203238N-phenethylpiperidone

Product 1

HCID 104940404-anilino-N-phenethylpiperidoneYield 50%

Procedure

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.

Sources & evidence

ORD record: ord-75542113e23746eb8562d511a7d26854
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399677B2

Linked notes

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