Sodium Iodide → Ziprasidone

HRID 1925221

Reaction equation

HRID 1925221 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.Cl.S1C2C=CC=CC=2C(N2CCNCC2)=N1.ClCCC1C=C2C(=CC=1Cl)NC(=O)C2.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C>[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

7

Reactant 5

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 219099Ziprasidone HydrochlorideHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Product 1

HCID 60854Ziprasidone

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

U.S. Pat. No. 4,831,031 discloses a process for the preparation of ziprasidone hydrochloride, which involves refluxing N-(1,2-benzisothiazol-3-yl)piperazine with 5-(2-chloroethyl)-6-chloro-oxindole in methyl isobutyl ketone in the presence of sodium iodide and sodium carbonate for about 40 hours followed by column chromatographic purification of the product to get ziprasidone base which is dissolved in methylene chloride and treated with ethereal hydrogen chloride to get ziprasidone hydrochloride salt. The salt is washed with acetone and the product is dried.

Workup

  1. customfollowed by column chromatographic purification of the product

Sources & evidence

ORD record
ord-a1fe5bcacab64580aac065d315eeeb4c
Source dataset
uspto-grants-2012_05
Patent number
US08178674B2

Linked notes

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