Duloxetine → Duloxetine Hydrochloride

HRID 2388366Notes

Reaction equation

HRID 2388366 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(O)(C)C>C(OC(C)C)(=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 21912024Isopropanol hydrochloride

Product 1

HCID 60834Duloxetine Hydrochloride

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Conditions

Temperature
7.5 °C

Procedure

Duloxetine free base (10 gm) was dissolved in isopropyl acetate (100 ml) and cooled to 5-10° C. To this solution isopropyl alcohol-HCl solution (about 15%) was added dropwise till pH was between 2-3. The resulting thick slurry stirred at 15-20° C. for two hours. Solid was filtered, washed with isopropyl acetate (20 ml), dried under reduced pressure at 45-50° C. Yield: 8.2 gm; chemical purity: 99.8% (by HPLC) and chiral purity: 99.95%.

Workup

  1. filtrationSolid was filtered
  2. washwashed with isopropyl acetate (20 ml)
  3. customdried under reduced pressure at 45-50° C

Sources & evidence

ORD record
ord-71e153f617644e8596c711ec7bbc15e0
Source dataset
uspto-grants-2012_09
Patent number
US08269023B2

Reaction notes

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