Ethyl Acetate → Paroxetine

HRID 2119785Notes

Reaction equation

HRID 2119785 reaction equation
CS(O)(=O)=O.[CH:6]1[C:11]([C@H:12]2[C@H:17]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][O:26][C:24]=4[CH:25]=3)[CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:10][CH:9]=[C:8]([F:29])[CH:7]=1.C(OCC)(=O)C>C(O)C>[CH:10]1[C:11]([C@H:12]2[C@H:17]([CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]4[O:28][CH2:27][O:26][C:24]=4[CH:25]=3)[CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:6][CH:7]=[C:8]([F:29])[CH:9]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 9845306Paroxetine methanesulfonate

Product 1

HCID 43815Paroxetine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the production of paroxetine mesylate, ethyl acetate or ethanol are the most suitable solvents for the salt formation. In an industrially suitable process, paroxetine obtained by the present process is dissolved in said solvent at increased temperature, preferably between 50° C. and 70° C. and methane sulphonic acid is added at the same temperature to the solution. The resulting solution is cooled to a temperature close to ambient, e.g. 20° C.-30° C., inoculated with a seeding crystal and cooled to about 0° C. After stirring at the same temperature for 0.5-3 hours, the solid product is filtered or centrifuged and washed with the same solvent. If necessary, the product may be recrystallized, advantageously from the same solvent.

Sources & evidence

ORD record
ord-ea4edef6747d4fef8bae24a8b3dd924b
Source dataset
uspto-grants-2004_02
Patent number
US06686473B2

Reaction notes

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