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

HRID 483668Notes

Reaction equation

HRID 483668 reaction equation
CC(N(C)C)=O.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.[CH3:18][NH:19][CH2:20][CH2:21][CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:23].[H-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:18][NH:19][CH2:20][CH2:21][CH:22]([O:23][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[ClH:7]

Participants

7

Reactant 4

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 27339893-Methylamino-1-phenylpropanol

Product 1

HCID 62857Fluoxetine hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
115 °C

Procedure

A mixture of dimethylacetamide (70 ml), toluene (20 ml), 4-chlorobenzotrifluoride (15 ml) and 3-methylamino-1-phenyl-1-propanol (15.6 ml) was heated to 115° C. A suspension of sodium hydride (6.2 g) in toluene (20 ml) was added gradually. The mixture was kept at 115° C. for 1 hour and cooled. Water (160 ml) and toluene (160 ml) were added. The phases were separated. The dried toluene phase was treated, with cooling, with gaseous hydrogen chloride. Fluoxetine hydrochloride (27.6 g) was precipitated. It was filtered and dried.

Workup

  1. additionwas added gradually
  2. temperaturecooled
  3. customThe phases were separated
  4. additionThe dried toluene phase was treated
  5. temperaturewith cooling, with gaseous hydrogen chloride
  6. customFluoxetine hydrochloride (27.6 g) was precipitated
  7. filtrationIt was filtered
  8. customdried

Sources & evidence

ORD record
ord-f69107d3687b4a6a81179b788470230b
Source dataset
uspto-grants-1993_07
Patent number
US05225585

Reaction notes

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