Potassium Iodide → (E)-3-{[1-(Ethoxycarbonylmethyl)pyrrol-2yl]methylidene]-1-(triphenylmethyl)piperidin-4-one

HRID 1171658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171658
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[CH2:8][N:9]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:11][C:12]\1=[O:13].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:38]([O:37][C:35]([CH2:34][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[CH:6]=[C:7]1\[CH2:8][N:9]([C:14]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:10][CH2:11][C:12]\1=[O:13])=[O:36])[CH3:39]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23138769(E)-3-[(Pyrrol-2-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one

Produkt 1

HCID 23138894(E)-3-{[1-(Ethoxycarbonylmethyl)pyrrol-2yl]methylidene]-1-(triphenylmethyl)piperidin-4-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (E)-3-[(pyrrol-2-yl)methylidene]-1-(triphenylmethyl)piperidin-4-one (7.16 g) and ethyl bromoacetate (8.60 g) in N,N-dimethylformamide (80 ml) were added potassium carbonate (7.10 g) and potassium iodide (8.50 g) with stirring at room temperature, and the resulting mixture was stirred at 80° C. for 4 hours. After filtration, the reaction mixture was diluted with dichloromethane, subsequently washed with saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate, hexane, and dichloromethane (1:2:1) as the eluent to afford the title compound (7.13 g, yield: 83%) as a yellow amorphous solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 80° C. for 4 hours
  2. filtrationAfter filtration
  3. additionthe reaction mixture was diluted with dichloromethane
  4. washsubsequently washed with saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-0f51927cf4a2469099f5cbeb736ced1d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829580B2

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