(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amine → (+-)-Duloxetine

HRID 2234231

Reaktionsgleichung

Reaktionsgleichung von HRID 2234231
C(O[K])(C)(C)C.[CH3:7][N:8]([CH2:10][CH2:11][C@@H:12]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)C>CS(C)=O>[CH3:7][NH:8][CH2:10][CH2:11][CH:12]([O:18][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 24739908(R)-N,N-dimethyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-amineHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 122252(+-)-DuloxetineAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

tBuOK (16.8 g) is added to a solution of (R)-N,N-dimethyl-3-(naphthyloxy)-3-(2-thienyl)propylamine (31 g) in DMSO (100 ml), bubbled with a moderate stream of nitrogen, and the mixture is stirred and heated at 110° C. for 2 hours. After cooling down to lab temperature, the mixture is diluted with water (300 ml) and the racemic product is extracted with toluene. After evaporation, 25 g (84%) of (RS)-N-methyl-3-(naphthyloxy)-3-(2-thienyl)propylamine is obtained.

Aufarbeitung

  1. custombubbled with a moderate stream of nitrogen
  2. temperatureAfter cooling down to lab temperature
  3. additionthe mixture is diluted with water (300 ml)
  4. extractionthe racemic product is extracted with toluene
  5. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-b7337c332b4c441e833ec95572d2cdcd
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709662B2

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