Ziprasidone Hydrochloride → Ziprasidone

HRID 1925222Notes

Reaction equation

HRID 1925222 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.ClCCC1C=C2C(=CC=1Cl)NC(=O)C2.S1C2C=CC=CC=2C(N2CCNCC2)=N1>C(=O)([O-])[O-].[Na+].[Na+]>[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

5

Reactant 3

HCID 219099Ziprasidone HydrochlorideHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 106094745-(2-Chloroethyl)-6-chlorooxindole

Product 1

HCID 60854Ziprasidone

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
20 °C

Procedure

U.S. Pat. No. 5,312,925 discloses a process for the preparation of ziprasidone hydrochloride, which involves heating to reflux a mixture of 5-(2-chloroethyl)-6-chloro-oxindole and 1-(1,2-benzisothiazol-3-yl)piperazine in aqueous sodium carbonate for 14 hours, followed by cooling to 20° C. and filtration. The wet product is re-slurried in isopropyl alcohol and filtered, washed with fresh isopropyl alcohol followed by drying under vacuum to get ziprasidone base. The base is then treated with aqueous hydrochloric acid in the presence of water at a temperature of about 60-65° C. for 3 to 24 hours, followed by filtration, washing with water and drying under vacuum to get ziprasidone hydrochloride.

Workup

  1. temperatureinvolves heating
  2. temperatureto reflux
  3. filtrationfiltration
  4. filtrationfiltered
  5. washwashed with fresh isopropyl alcohol
  6. customby drying under vacuum

Sources & evidence

ORD record
ord-b3fe1195cc804f14a815670a0b6e0aac
Source dataset
uspto-grants-2012_05
Patent number
US08178674B2

Reaction notes

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