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

HRID 2234231Notes

Reaction equation

HRID 2234231 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 122252(+-)-DuloxetineYield 84.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b7337c332b4c441e833ec95572d2cdcd
Source dataset
uspto-grants-2010_05
Patent number
US07709662B2

Reaction notes

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