Ammonium → Duloxetine

HRID 1714409Notes

Reaction equation

HRID 1714409 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12)[C:6]1[S:10][CH:9]=[CH:8][CH:7]=1.C([O-])(=O)C([O-])=O.[NH4+]>C(OCC)(=O)C.O>[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12)[C:6]1[S:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 223AmmoniumHCID 86618017HCID 86618017, compound

Product 1

HCID 60835DuloxetineYield 87.1%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

Duloxetine oxalate (38.7 g) was placed into 300 ml of an ethyl acetate/water (1:1) mixture. Aqueous ammonium solution was added to dissolve the solid completely under stirring. The separated aqueous layer was washed with ethyl acetate twice. The combined organic solution was then washed with saturated brine, and dried with anhydrous sodium sulphate. The free duloxetine (26 g) was obtained as an oil by removing the solvents from the filtrate solution.

Workup

  1. dissolutionto dissolve the solid completely
  2. washThe separated aqueous layer was washed with ethyl acetate twice
  3. washThe combined organic solution was then washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulphate

Sources & evidence

ORD record
ord-a90d032050054b5f972658fdae3db6bf
Source dataset
uspto-grants-2010_09
Patent number
US07795454B2

Reaction notes

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