Water → 2-{2-[2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide

HRID 1789351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789351
[N-:1]=[C:2]=[O:3].[K+].O.[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]3[NH:32][CH2:31][CH2:30][S:29]3)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1.C(=O)(O)[O-].[Na+]>C(O)C.C(O)(=O)C>[F:6][C:7]1[CH:8]=[C:9]([N:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH:28]3[N:32]([C:2]([NH2:1])=[O:3])[CH2:31][CH2:30][S:29]3)[CH2:15][CH2:14]2)[CH:10]=[CH:11][CH:12]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 11051572Potassio isocyanate2×HCID 13768101HCID 13768101, Verbindung

Produkt 1

HCID 137680352-{2-[2-(4-(3-Fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamideAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.12 g of potassium isocyanate, 10 ml of water and 2 ml of acetic acid is added to a solution of 2.68 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine in 20 ml of ethanol, and the mixture is stirred at room temperature for 2 hours. A mixture of 0.56 g of potassium isocyanate and 0.5 ml of acetic acid is added to said mixture, and the mixture is stirred at the same temperature for 2 hours. The mixture is made alkaline with sodium bicarbonate and concentrated under reduced pressure to remove solvent. The residue is extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel chromatograph (solvent, ethyl acetate), and the resultant product is recrystallized from a mixture of ethyl acetate and ether. 2.6 g of 2-{2-[2-(4-(3-fluorophenyl)piperazin-1-yl)ethyloxy]phenyl}thiazolidine-3-carboxamide are obtained.

Aufarbeitung

  1. additionis added
  2. stirringthe mixture is stirred at the same temperature for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. customto remove solvent
  5. extractionThe residue is extracted with ethyl acetate
  6. washThe extract is washed with a saturated sodium chloride solution
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove solvent
  10. customThe residue is purified by silica gel chromatograph (solvent, ethyl acetate)
  11. customthe resultant product is recrystallized from a mixture of ethyl acetate and ether

Quellen und Nachweise

ORD-Eintrag
ord-999349dc79214221aaf430c3096dbad1
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689327

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