Hydrochloric Acid → Ziprasidone Hydrochloride

HRID 1925225Notes

Reaction equation

HRID 1925225 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:29]CCl.Cl>CC(C)=O>[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 6344DichloromethaneHCID 60854Ziprasidone

Product 1

HCID 219099Ziprasidone Hydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
32.5 °C

Procedure

To substantially pure ziprasidone base (100 g), was added dichloromethane (2.0 Lit) and stirred for 15-20 minutes at 30-35° C. To this, ethereal solution of hydrogen chloride (95.7 ml) was added over a period of 5-10 min at 30-35° C. under stirring. The suspension was further stirred for 17-20 hours at 32-35° C. and separated solids were filtered under vacuum and nitrogen atmosphere at 32-35° C. The wet solid was washed with diethyl ether (100 ml). The wet cake so obtained was suspended in acetone (500 ml) at 30-35° C. and stirred for 15-20 minutes at 30-35° C. The solid was filtered, washed with acetone (0.20 Lit) and dried under vacuum at 55-60° C. for 12-15 hours till the moisture content was not more than 0.5% w/w.

Workup

  1. stirringunder stirring
  2. stirringThe suspension was further stirred for 17-20 hours at 32-35° C.
  3. customseparated solids
  4. filtrationwere filtered under vacuum and nitrogen atmosphere at 32-35° C
  5. washThe wet solid was washed with diethyl ether (100 ml)
  6. customThe wet cake so obtained
  7. stirringstirred for 15-20 minutes at 30-35° C
  8. filtrationThe solid was filtered
  9. washwashed with acetone (0.20 Lit)
  10. customdried under vacuum at 55-60° C. for 12-15 hours till the moisture content

Sources & evidence

ORD record
ord-dd417107a1884755a486bf53c10d9ca3
Source dataset
uspto-grants-2012_05
Patent number
US08178674B2

Reaction notes

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