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 482054Notes

Reaction equation

HRID 482054 reaction equation
[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

Participants

3

Reactant 1

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

Product 1

HCID 190650841-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,3-piperazinedioneYield 36.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e8708d30370c436e84fb04e2706c3608
Source dataset
uspto-grants-1998_08
Patent number
US05792780

Reaction notes

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