Methanesulfonic Acid → Ziprasidone mesylate

HRID 2185112Notes

Reaction equation

HRID 2185112 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[S:9][N:8]=[C:7]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][C:18]4[CH:19]=[C:20]5[CH2:28][C:26](=[O:27])[NH:25][C:21]5=[CH:22][C:23]=4[Cl:24])[CH2:12][CH2:11]3)[C:5]=2[CH:6]=1.[CH3:29][S:30]([OH:33])(=[O:32])=[O:31]>C(O)(C)C>[CH3:29][S:30]([OH:33])(=[O:32])=[O:31].[CH:1]1[CH:2]=[CH:3][C:4]2[S:9][N:8]=[C:7]([N:10]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][C:18]4[CH:19]=[C:20]5[CH2:28][C:26](=[O:27])[NH:25][C:21]5=[CH:22][C:23]=4[Cl:24])[CH2:14][CH2:15]3)[C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 60854Ziprasidone

Product 1

HCID 154068Ziprasidone mesylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1 g of ziprasidone free base was added to 20 mL of isopropyl alcohol, followed by 140 mg of methanesulfonic acid. After a few minutes the slurry which formed thickened and lightened somewhat in color as it precipitated. The salt was harvested by filtration through a 5 μm polytetrafluoroethylene membrane.

Workup

  1. customAfter a few minutes the slurry which formed
  2. customprecipitated
  3. filtrationThe salt was harvested by filtration through a 5 μm polytetrafluoroethylene membrane

Sources & evidence

ORD record
ord-033bf44b26ce437cb4fff9d0008623f5
Source dataset
uspto-grants-2002_06
Patent number
US06399777B2

Reaction notes

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