Acetyl chloride → N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid

HRID 1789358Notes

Reaction equation

HRID 1789358 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:23]3[N:27]([C:28]([NH2:30])=[O:29])[CH2:26][CH2:25][S:24]3)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:38](Cl)(=[O:40])[CH3:39].[O:42]1CC[CH2:44][CH2:43]1>>[C:38]([N:30]=[C:28]([N:27]1[CH2:26][CH2:25][S:24][CH:23]1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:9][CH2:10]1)[O:29][C:43](=[O:42])[CH3:44])(=[O:40])[CH3:39]

Participants

5

Reactant 4

HCID 6367Acetyl chloride2×HCID 8028Tetrahydrofuran2×HCID 8471Triethylamine2×HCID 137680352-{2-[2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

Product 1

HCID 20188172N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acidYield 56%

Procedure

1.08 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are dissolved in 20 ml of tetrahydrofuran, and 0.76 g of triethylamine is added thereto. A solution of 0.59 g of acetyl chloride in one ml of tetrahydrofuran is added to the mixture under ice-cooling, and the mixture is stirred at room temperature for 3 days. 0.59 g of acetyl chloride and 0.76 g of triethylamine are added to the mixture, and the mixture is stirred at room temperature for 24 hours. The mixture is concentrated under reduced pressure to remove solvent. The residue is dissolved in ethyl acetate, and the solution is washed with a saturated sodium chloride solution, an aqueous sodium bicarbonate solution and a sodium chloride solution, successively. The ethyl acetate solution is dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=2:1). The eluate is concentrated under reduced pressure to remove solvent, and the residue is recrystallized from a mixture of chloroform and ether. 0.72 g of N,O-diacetyl-2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboximidic acid is obtained. Yield: 56%.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 24 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto remove solvent
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washthe solution is washed with a saturated sodium chloride solution
  7. dry with materialThe ethyl acetate solution is dried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatography (solvent, chloroform:ethyl acetate=2:1)
  11. concentrationThe eluate is concentrated under reduced pressure
  12. customto remove solvent
  13. customthe residue is recrystallized from a mixture of chloroform and ether

Sources & evidence

ORD record
ord-7c55a82908a04847bac89c1a561b1980
Source dataset
uspto-grants-1987_08
Patent number
US04689327

Reaction notes

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