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

HRID 1696759

Reaktionsgleichung

Reaktionsgleichung von HRID 1696759
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3]1.Cl[CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:17][N:16]([CH3:18])[C:14](=[O:15])[CH2:13][O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:2]([CH3:1])[CH:3]=[CH:4]2

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 221368021-methyl-1H-indol-7-ol

Produkt 1

HCID 67274369N,N-Dimethyl-2-(1-methyl-1H-indol-7-yloxy)-acetamideAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-1-H-indol-7-ol (Chemstep, CAS: 47577-33-4, 2.2 g, 15 mmol) and 2-chloro-N,N-dimethylacetamide (Fluka, CAS: 2675-89-0, 2.0 g, 17 mmol) in acetone (25 mL) were added potassium carbonate (2.5 g, 18 mmol) and potassium iodide, (0.25 g, 1.5 mmol). The reaction mixture was stirred at reflux for 4 h, quenched with ice/water, and extracted with ethyl acetate. The organics were washed, dried and concentrated. The residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain the desired compound (2.9 g) as a creamy solid. MS (ISP): m/e 233.1 (M+H)+

Aufarbeitung

  1. temperatureat reflux for 4 h
  2. customquenched with ice/water
  3. extractionextracted with ethyl acetate
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fc01a8f850df47e78e39972ea3c7f8fc
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163778B2

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