Potassium Iodide → N,N-diethyl-2-(1H-indol-7-yloxy)acetamide

HRID 1351918

Reaktionsgleichung

Reaktionsgleichung von HRID 1351918
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:19]([CH2:24][CH3:25])[C:20](=[O:23])[CH2:21]Cl)[CH3:18].[I-].[K+]>CC(C)=O>[CH2:17]([N:19]([CH2:24][CH3:25])[C:20](=[O:23])[CH2:21][O:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2)[CH3:18]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 16844Chloro-N,N-diethylacetamideHCID 27376517-Hydroxyindole

Produkt 1

HCID 11357035N,N-diethyl-2-(1H-indol-7-yloxy)acetamideAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 7-hydroxyindole (2.65 g, 20 mmol) in acetone (20 ml) are added potassium carbonate (3.32 g), chloroacetic acid diethylamide (3.29 g, 22 mmol) and potassium iodide (0.33 g), and the mixture is refluxed for 4 hours. After cooling with ice, the insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure to remove the solvent. To the residue are added chloroform (40 ml) and water (20 ml), and the mixture is stirred. The chloroform layer is separated, and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and isopropyl ether (100 ml) is added to the residue. The precipitated crystals are collected by filtration, and dried to give the title compound N,N-diethyl-2-(1H-indol-7-yloxy)acetamide (4.37 g, yield: 89%) as white crystals.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling with ice
  3. customthe insoluble materials are removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto remove the solvent
  6. additionTo the residue are added chloroform (40 ml) and water (20 ml)
  7. customThe chloroform layer is separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent is evaporated under reduced pressure, and isopropyl ether (100 ml)
  10. additionis added to the residue
  11. filtrationThe precipitated crystals are collected by filtration
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a23fcec7b3ee4a95b690e1add82108da
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217724B2

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