Hydrochloric Acid → Duloxetine Hydrochloride

HRID 2060926Notes

Reaction equation

HRID 2060926 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>[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 313Hydrochloric Acid2×HCID 60835Duloxetine

Product 1

HCID 60834Duloxetine Hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

According to prior art methods, duloxetine free base is treated with hydrochloric acid in the presence of ester or ketone solvents. The prior art methods employ hydrochloric acid in concentrated form, in diluted forms with ethyl acetate, or as a gas. The solid obtained is isolated by concentration and/or filtration, which is subsequently washed and dried to obtain duloxetine hydrochloride. Washing is generally carried out to remove the soluble by-products and drying is finally carried out to remove the residual solvents. The present inventors have observed that even after usual washing and drying steps, the finally obtained duloxetine hydrochloride is contaminated with 4-[3-(methylamino)-1-thiophen-2-ylpropyl]naphthalen-1-ol of Formula II in undesirable amounts.

Workup

  1. customThe solid obtained
  2. customis isolated by concentration and/or filtration, which
  3. washis subsequently washed
  4. customdried

Sources & evidence

ORD record
ord-3035b00856bc4251b7925ae0148b1fc7
Source dataset
uspto-grants-2012_10
Patent number
US08278463B2

Reaction notes

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