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1-Chloro-4-(trifluoromethyl)benzene → Fluoxetine

HRID 374359
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HRID 374359 반응식
[H][H].[C:3]1([CH:9]([OH:14])[CH2:10][CH2:11][NH:12][CH3:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1.CC(C)([O-])C.[K+]>C(OCC)(=O)C.[Pt].[Pd].[Pd].[Pt].CS(C)=O.CN1CCCC1=O>[CH3:13][NH:12][CH2:11][CH2:10][CH:9]([O:14][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 4

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 27339893-Methylamino-1-phenylpropanol3회HCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 3386Fluoxetine수율 85%

시약·촉매·용매 6

HCID 23938Palladium
촉매
HCID 23939Platinum촉매
HCID 56923625Palladium--platinum (1/1)촉매
HCID 679Dimethyl Sulfoxide용매
HCID 8857Ethyl Acetate용매
HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.

후처리

  1. customis formed

출처 및 근거

ORD 기록
ord-3db2d2cfcc484cf4876ef3b9d4ac9f82
출처 데이터셋
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05166437

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