Sodium Iodide → Ziprasidone

HRID 1724632Notes

Reaction equation

HRID 1724632 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[Cl:13])[NH:9][C:8](=[O:14])[CH2:7]2.[N:15]1([C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[S:23][N:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1CCCCC1>[CH:27]1[CH:28]=[CH:29][C:24]2[S:23][N:22]=[C:21]([N:15]3[CH2:16][CH2:17][N:18]([CH2:2][CH2:3][C:4]4[CH:5]=[C:6]5[CH2:7][C:8](=[O:14])[NH:9][C:10]5=[CH:11][C:12]=4[Cl:13])[CH2:19][CH2:20]3)[C:25]=2[CH:26]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Product 1

HCID 60854ZiprasidoneYield 87.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

Refluxed the reaction mixture of 5-(2-chloroethyl)-6-chloro oxindole (100 gm), 3-(1-piperazinyl)-1,2-benzisothiazole (104.7 gm), sodium carbonate (92.2 gm), sodium iodide (6.4 gm), tetra butyl ammonium bromide (28 gm) and cyclohexane (1000 mL) till the reaction was completed. The reaction mass was cooled to a temperature of 30° C. and the solid was filtered. To the wet compound was added water (1000 mL) and continued stirring for 45 minutes. The solid was filtered and washed with water (100 mL). To the water wet compound was added acetone (500 mL) and there was stirring for 2 hours at room temperature. The compound was filtered and washed with acetone (200 mL) and dried at a temperature of 70-75° C. to afford the Crude Ziprasidone base (156.9 g)

Workup

  1. temperatureRefluxed
  2. filtrationthe solid was filtered
  3. additionTo the wet compound was added water (1000 mL)
  4. filtrationThe solid was filtered
  5. washwashed with water (100 mL)
  6. additionTo the water wet compound was added acetone (500 mL) and there
  7. stirringwas stirring for 2 hours at room temperature
  8. filtrationThe compound was filtered
  9. washwashed with acetone (200 mL)
  10. customdried at a temperature of 70-75° C.

Sources & evidence

ORD record
ord-7a0be2e97a63469392a60210136bb75d
Source dataset
uspto-grants-2009_02
Patent number
US07488729B2

Reaction notes

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