Toluene → Fluoxetine

HRID 374357

Reaktionsgleichung

Reaktionsgleichung von HRID 374357
C[C:2]([CH3:5])([O-:4])[CH3:3].[K+].[CH3:7][N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=O.ClC1C=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17]C=1.[C:25]1(C)[CH:30]=[CH:29]C=[CH:27][CH:26]=1>O>[CH3:7][NH:8][CH2:9][CH2:10][CH:11]([C:12]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)[O:4][C:2]1[CH:5]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:3]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 13387N-methyl-2-pyrrolidoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 3386Fluoxetine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 4.0 g (0.0357 mol) potassium t-butoxide, 30 ml of N-methylpyrrolidone, 5.0 g (0.0303 mol) of 1-phenyl-3-N-methylaminopropan-1-ol and 7.4 g (0.0410 mol) of 1-chloro-4-trifluoromethylbenzene was heated to 140° C. and the reaction mixture was agitated at this temperature for 3 hours. The mixture was then cooled to 20°-25° C. and 40 ml of toluene and 60 ml of water were added. The layers were separated and water-phase was extracted with 40 ml of toluene. The combined toluene-phases were washed four times with 20 ml of water. Toluene was evaporated under reduced pressure yielding 7.19 g of the product.

Aufarbeitung

  1. temperatureThe mixture was then cooled to 20°-25° C.
  2. customThe layers were separated
  3. extractionwater-phase was extracted with 40 ml of toluene
  4. washThe combined toluene-phases were washed four times with 20 ml of water
  5. customToluene was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b34bae52177e4aeaa7f77a82ff9cb36a
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166437

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