Potassium Carbonate → Ziprasidone

HRID 13566

Reaction equation

HRID 13566 reaction equation
[N:1]1([C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[S:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][C:22](=[O:26])[NH:23]2)=[CH:19][C:18]=1[CH2:27][CH2:28]Cl.C(=O)([O-])[O-].[K+].[K+]>[I-].[K+].O>[S:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:28][CH2:27][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][C:17]=3[Cl:16])[NH:23][C:22](=[O:26])[CH2:21]4)[CH2:3][CH2:2]2)=[N:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Product 1

HCID 60854ZiprasidoneYield 75%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a 50 ml 3 necked round bottom flask there were placed 1 gram (4.56 mmol) of 3-piperazinylbenzo[d]isothiazole; 2.5 grams (10.86 mmol) of 6-chloro-5-(2-chloroethyl)indolin-2-one; 50 mg of potassium iodide; 1.64 grams (11.88 mmol) of potassium carbonate. The contents of the flask were heated to 90° C. The reaction was monitored by HPLC. After completion of the reaction, 50 ml of DM water was added to the reaction mixture and stirred. The product was filtered off and washed with water and dried to obtain 1.41 grams (75%) of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one. The crude product was purified by IPA and/or THF. The product matched the spectra of a standard NMR and showed the correct retention time by HPLC with 98.0% assay. The melting point of the compound was found to be 218° C.-220° C., and was found to conform with the melting point of 218° C.-220° C. as disclosed in U.S. Pat. No. 5,206,366.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationThe product was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b5f3008da549441db70ddf038fe579ea
Source dataset
uspto-grants-2010_06
Patent number
US07728136B2

Linked notes

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