Hydrogen Peroxide → 3-{4-[2-(6-Chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)ethyl]piperazin-1-yl}-1H-1lambda~4~,2-benzothiazol-1-one

HRID 1796187Notes

Reaction equation

HRID 1796187 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.[OH:29]O>C(#N)C>[CH2:14]1[N:13]([CH2:16][CH2:17][C:18]2[CH:19]=[C:20]3[CH2:28][C:26]([NH:25][C:21]3=[CH:22][C:23]=2[Cl:24])=[O:27])[CH2:12][CH2:11][N:10]([C:7]2[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[S:9](=[O:29])[N:8]=2)[CH2:15]1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 60854Ziprasidone

Product 1

HCID 159594073-{4-[2-(6-Chloro-2-oxo-2,3-dihydro-1H-indol-5-yl)ethyl]piperazin-1-yl}-1H-1lambda~4~,2-benzothiazol-1-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ziprasidone made as described in Example 1 (0.70 g, 1.7 mmol) in acetonitrile is added 30% H2O2 (1.7 mmol). After stirring for 24 hours at room temperature, the reaction mixture is cooled, filtered, and evaporated. The residue is chromatographed on silica gel, eluting the by-products with ethyl acetate (1 L) and the product with 4% methanol in ethyl acetate (1.5 L). The product fractions are evaporated, taken up in methylene chloride, and precipitated by addition of ether saturated with HCl; the solid is filtered and washed with ether, dried, and washed with acetone.

Workup

  1. temperaturethe reaction mixture is cooled
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue is chromatographed on silica gel
  5. washeluting the by-products with ethyl acetate (1 L)
  6. customThe product fractions are evaporated
  7. customprecipitated by addition of ether saturated with HCl
  8. filtrationthe solid is filtered
  9. washwashed with ether
  10. customdried
  11. washwashed with acetone

Sources & evidence

ORD record
ord-30a40c9347be4827bdaecac9e905cd58
Source dataset
uspto-grants-2006_04
Patent number
US07030142B1

Reaction notes

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