Duloxetine → Duloxetine Hydrochloride

HRID 2388365Notes

Reaction equation

HRID 2388365 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.[ClH:22].C(OCC)(=O)C>C(OCC)(=O)C>[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.[ClH:22]

Participants

4

Reactant 2

HCID 60835DuloxetineHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 60834Duloxetine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
7.5 °C

Procedure

Duloxetine free base (35 gm) was dissolved in ethyl acetate (500 ml) and the resulting solution was cooled to 5-10° C. To this solution was added to ethyl acetate-HCl solution (about 12%) dropwise in 10-15 minutes. Slowly white solid started to precipitate out. Addition of ethyl acetate-HCl solution was continued till the pH of slurry reached between 2-3. The thick slurry mass was stirred at 15-20° C. for one hour. Solid was filtered, washed with ethyl acetate and dried under reduced pressure at 45-50° C. Yield: 35.3 gm, chemical purity: 99.8% (by HPLC) and chiral purity: 99.95% (by HPLC).

Workup

  1. customto precipitate out
  2. additionAddition of ethyl acetate-HCl solution
  3. filtrationSolid was filtered
  4. washwashed with ethyl acetate
  5. customdried under reduced pressure at 45-50° C

Sources & evidence

ORD record
ord-0e3df7f2c4ca42b0a1ee23cc5c50b2ef
Source dataset
uspto-grants-2012_09
Patent number
US08269023B2

Reaction notes

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