N-ethoxalyl-N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline → 1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,3-piperazinedione

HRID 482054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482054
[C:1]([N:8]([CH2:23][CH2:24][N:25]1C(=O)C2=CC=CC=C2[C:26]1=[O:35])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:22])([F:21])[CH:18]([F:20])[F:19])=[CH:11][CH:10]=1)(C(OCC)=O)=[O:2]>C(O)C>[F:21][C:17]([F:22])([CH:18]([F:20])[F:19])[CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:1]2=[O:2])=[CH:10][CH:11]=1

Komponenten

3

Edukt 1

HCID 86749721N-ethoxalyl-N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline

Produkt 1

HCID 190650841-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,3-piperazinedioneAusbeute 36,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of the obtained N-ethoxalyl-N-(2-phthalimido)ethyl-4-(2,2,3,3-tetrafluoropropoxy)aniline (3.4 g), hydradine hydrate (0.7 ml) and ethanol (80 ml) was refluxed for 9 hours. The crystals separated out were filtered off before cooling and the solvent of the filtrate was distilled off under reduced pressure. Water (150 ml) and ethyl acetate (300 ml) were added to the residue to fractionate. The ethyl acetate layer was washed with 5% aqueous solution of sodium bicarbonate and then with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent; ethyl acetate:dichloromethane: methanol=7:7:1 v/v) to give 1-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2,3-piperazinedione (0.8 g) as a colorless powder.

Aufarbeitung

  1. temperaturewas refluxed for 9 hours
  2. customThe crystals separated out
  3. filtrationwere filtered off
  4. temperaturebefore cooling
  5. distillationthe solvent of the filtrate was distilled off under reduced pressure
  6. additionWater (150 ml) and ethyl acetate (300 ml) were added to the residue
  7. washThe ethyl acetate layer was washed with 5% aqueous solution of sodium bicarbonate
  8. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by silica gel chromatography (eluent; ethyl acetate:dichloromethane: methanol=7:7:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-e8708d30370c436e84fb04e2706c3608
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792780

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