Hydrochloric Acid → Ziprasidone Hydrochloride

HRID 2243899Notes

Reaction equation

HRID 2243899 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.[ClH:29].CO>ClC1C=CC=CC=1>[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.[ClH:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 60854Ziprasidone

Product 1

HCID 219099Ziprasidone Hydrochloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a slurry of ziprasidone base Form B (10 g) in monochlorobenzene (100 ml) was added aqueous HCl (37%) (10 ml) at room temperature and the stirring was continued at room temperature over night. A sticky solid was formed, to which methanol (50 ml) was added, followed by stirring for an additional 4 hours. The solid was filtered and washed with methanol. The wet product was crystalline ziprasidone HCl as confirmed by XRD. After drying at 50° C. for about 16 hours, crystalline ziprasidone HCl Form A was obtained (10.37 g) as confirmed by XRD (The water content was 4.17% by K.F.).

Workup

  1. waitthe stirring was continued at room temperature over night
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with methanol
  5. customAfter drying at 50° C. for about 16 hours

Sources & evidence

ORD record
ord-85502828b5e6453788a434172b61929d
Source dataset
uspto-grants-2010_03
Patent number
US07678799B2

Reaction notes

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