Hydrochloric Acid → Duloxetine Hydrochloride

HRID 1694626

Reaction equation

HRID 1694626 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]>CC(C)=O.C(OCC)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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60835Duloxetine

Product 1

HCID 60834Duloxetine HydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Duloxetine base (99% ee, 0.5 g, 1.68 mmoles) was dissolved in acetone (5 mL) and stirred with cooling in an ice-water bath. Hydrochloric acid in diethyl ether (2M, 0.8 mL) was added, and a precipitate formed within 2 minutes. The mixture was stirred at ambient temperature 16 hours, filtered and the collected solid washed with acetone (0.5 mL). The white solid was then dried under vacuum at ambient temperature to yield duloxetine hydrochloride (0.485 g, 1.45 mmoles, yield: 86%; Chiral HPLC: 99.5% ee).

Workup

  1. temperaturewith cooling in an ice-water bath
  2. customa precipitate formed within 2 minutes
  3. stirringThe mixture was stirred at ambient temperature 16 hours
  4. filtrationfiltered
  5. washthe collected solid washed with acetone (0.5 mL)
  6. customThe white solid was then dried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-503f92caa39a48a5874a234db96d37b6
Source dataset
uspto-grants-2012_04
Patent number
US08158808B2

Linked notes

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