Acetic Acid → Ziprasidone Hydrochloride

HRID 1711975

Reaction equation

HRID 1711975 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.C(O)(=O)C.[ClH:33].O>C(O)(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.[ClH:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 60854Ziprasidone

Product 1

HCID 219099Ziprasidone Hydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
47.5 °C

Procedure

Ziprasidone (5 g) and 50 mL of acetic acid were placed into a round bottom flask and heated to 45-50° C. Added was 25 mL of aqueous hydrochloric acid slowly to the mixture over 20 min. Then the reaction mixture was refluxed. Water (10 mL) was added, followed by addition of 50 mL of Isopropanol. The reaction mass was cooled to 50° C. and distilled off the solvent completely under vacuum. The material formed was scratched from the flask.

Workup

  1. additionAdded
  2. customover 20 min
  3. temperatureThen the reaction mixture was refluxed
  4. temperatureThe reaction mass was cooled to 50° C.
  5. distillationdistilled off the solvent completely under vacuum
  6. customThe material formed

Sources & evidence

ORD record
ord-36d1abf674464e1b903451edb8e95ec6
Source dataset
uspto-grants-2010_09
Patent number
US07790886B2

Linked notes

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