Potassium Carbonate → HCID 67974754, Verbindung

HRID 2174471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174471
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH2:4].C([O-])([O-])=O.[K+].[K+].[CH3:24]/[C:25](=[CH:29]\[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[C:26](Cl)=[O:27]>CC(C)=O.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:5][C:3]=1[NH:4][C:26](=[O:27])/[C:25](/[CH3:24])=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 5706529HCID 5706529, VerbindungHCID 67975039HCID 67975039, Verbindung

Produkt 1

HCID 67974754HCID 67974754, VerbindungAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

2-chloro-5-(2-piperidinoethoxy)aniline (705 mg, 3.9 mmol, 1 eq.) was placed in a mixture of acetone (653 μL) and water (852 μL) in the presence of K2CO3 (1.1 g, 7.8 mmol, 2 eq.). (E)-2-methyl-3-phenylacryloyl chloride (705 mg, 3.9 mmol, 1 eq.) was then added at 0° C. The reaction mixture was allowed to warm-up to room temperature, stirred for 2 hours and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel to afford (E)-N-(2-chloro-5-(2-(piperidin-1-yl)ethoxy)phenyl)-2-methyl-3-phenylacrylamide (500 mg, 66%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-34526370d08d4451b3e4cbf8eb082a81
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061999B2

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