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

HRID 377950Notes

Reaction equation

HRID 377950 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:6].Cl[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1>>[CH3:1][NH:2][CH2:3][CH2:4][C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[O:6][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 7439089(S)-3-(Methylamino)-1-phenylpropan-1-ol

Product 1

HCID 1548968(S)-Fluoxetine

Procedure

A process according to claim 4 comprising the additional step, following all preceding steps, of reacting (S)-3-(methylamino)-1-phenylpropanol with a strong base followed by 4-chlorobenzotrifluoride to provide (S)-N-methyl-3-phenyl-3-[(α,α,α-trifluoro-p-tolyl)oxy]propylamine.

Sources & evidence

ORD record
ord-4927b50dcf974098aa36c6d0756a7e24
Source dataset
uspto-grants-2000_02
Patent number
US06028224

Reaction notes

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