Methanesulfonic Acid → Paroxetine Impurity 10

HRID 1108012

Reaction equation

HRID 1108012 reaction equation
[CH:1]1[C:6]([C@H:7]2[C@H:12]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]4[O:23][CH2:22][O:21][C:19]=4[CH:20]=3)[CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:5][CH:4]=[C:3](F)[CH:2]=1.[CH3:25][S:26]([OH:29])(=[O:28])=[O:27].CCCCCC>CC(O)C>[CH3:25][S:26]([OH:29])(=[O:28])=[O:27].[CH2:8]1[C@@H:7]([C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=2)[C@H:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][O:21][C:19]=3[CH:20]=2)[CH2:11][NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8058HexaneHCID 43815Paroxetine

Product 1

HCID 206527Paroxetine Impurity 10

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of paroxetine base (20.9 g) in propan-2-ol (70 ml) was added methanesulfonic acid (3.7 ml) in propan-2-ol (10 ml). The solution was heated to 50° C. and added portion-wise to hexane (200 ml) also at 50° C. The solution was stirred vigorously to form a precipitate which was stirred further to ensure crystallisation. The precipitate was collected by filtration, washed with hexane (40 ml) and dried in a vacuum desiccator over phosphorus pentoxide to give paroxetine methanesulfonate as a white crystalline solid.

Workup

  1. customto form a precipitate which
  2. stirringwas stirred further
  3. customcrystallisation
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with hexane (40 ml)
  6. dry with materialdried in a vacuum desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-a766c403ed2d4e2dadb43fd083a559ad
Source dataset
uspto-grants-2000_05
Patent number
US06063927

Linked notes

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