Fentanyl → 4-anilino-N-phenethylpiperidone

HRID 1948975

反応式

HRID 1948975 の反応式
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

参加物

4

反応物 3

HCID 3345FentanylHCID 6115AnilineHCID 12203238N-phenethylpiperidone

生成物 1

HCID 104940404-anilino-N-phenethylpiperidone収率 50%

実験手順

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.

出典と根拠

ORDレコード
ord-75542113e23746eb8562d511a7d26854
出典データセット
uspto-grants-2013_03
特許番号
US08399677B2

関連ノート

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