Potassium Carbonate → Ziprasidone

HRID 13567

Reaktionsgleichung

Reaktionsgleichung von HRID 13567
[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+].S1(CCCC1)(=O)=O>[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

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 31347SulfolaneHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Produkt 1

HCID 60854ZiprasidoneAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

In glass-lined reactor placed 21.1 Kg (96.34 mole) of 3-piperazinylbenzo[d]isothiazole; 31 kg (134.7 moles) of 6-chloro-5-(2-chloroethyl)indolin-2-one; 1.1 kg of potassium iodide; 20.0 kg (111.92 mole) of potassium carbonate and 63.2 lit of sulfolane. The contents of the flask were initially heated to 75° C. to 80° C. for 2 hrs. Then temperature was raised to 95° C. to 100° C. and stirred till completion of the reaction. After completion of the reaction 210 lit of DM water was added to the reaction mixture and stirred. The product was filtered off and washed with water and dried to obtain 29.75 kg of 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one (Ziprasidone).

Aufarbeitung

  1. customIn glass-lined reactor placed
  2. temperatureThe contents of the flask were initially heated to 75° C. to 80° C. for 2 hrs
  3. temperatureThen temperature was raised to 95° C. to 100° C.
  4. additionwas added to the reaction mixture
  5. stirringstirred
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1f25ff321e514b58b4c5fca27a5d1686
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728136B2

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