Hydrochloric Acid → N-acetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789359Notes

Reaction equation

HRID 1789359 reaction equation
[C:1]([N:4]=[C:5]([N:10]1[CH2:14][CH2:13][S:12][CH:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH2:26][CH2:25]1)[O:6]C(=O)C)(=[O:3])[CH3:2].Cl>C(O)C.O1CCCC1.[OH-].[Na+]>[C:1]([NH:4][C:5]([N:10]1[CH2:14][CH2:13][S:12][CH:11]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:22][CH2:23][N:24]1[CH2:25][CH2:26][N:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[CH2:28][CH2:29]1)=[O:6])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 20188172N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid

Product 1

HCID 13768046N-acetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideYield 90.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.59 g of N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid is dissolved in a mixture of 15 ml of ethanol and 5 ml of tetrahydrofuran, and 1.34 ml of 10% aqueous sodium hydroxide solution is added thereto under ice-cooling. The mixture is stirred for 15 minutes, and the mixture is neutralized with 10% hydrochloric acid. The mixture is concentrated under reduced pressure to remove solvent. The residue is extracted with ethyl acetate, and the extract is washed with an aqueous sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of ethyl acetate and ether. 0.49 g of N-acetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide is obtained.

Workup

  1. additionis added
  2. temperatureunder ice-cooling
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto remove solvent
  5. extractionThe residue is extracted with ethyl acetate
  6. washthe extract is washed with an aqueous sodium chloride solution
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is recrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-d0bb55d299664209bdb4fb168a9ad2a8
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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