Piperidine → 3-Isopropylidene-4-methoxy-1,3-dihydro-indol-2-one

HRID 2416934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416934
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6](=[O:12])[NH:7]2.N1CC[CH2:16][CH2:15][CH2:14]1>CC(C)=O>[C:15](=[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[O:2][CH3:1])[NH:7][C:6]1=[O:12])([CH3:16])[CH3:14]

Komponenten

4

Edukt 2

HCID 8082PiperidineHCID 5960014-Methoxy-2-indolinone

Produkt 1

HCID 219232453-Isopropylidene-4-methoxy-1,3-dihydro-indol-2-oneAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxyoxindole (3.0 g, 18.4 mmol) and piperidine (3.5 mL, 36.89 mmol) in acetone (100 mL) is heated at reflux for 18 hours. The mixture is concentrated to dryness and triturated with methanol (20 mL). Filtration removed 800 mg of unreacted 4-methoxyoxindole. The filtrate is preadsorbed on silica gel (5 g), and purified by flash chromtography (120 g SiO2, 25% ethyl acetate:hexane to 50% ethyl acetate:hexane) to provide 700 mg (19%) of 3-isopropylidene-4-methoxy-1,3-dihydro-indol-2-one. MS (ESI+) 204.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe mixture is concentrated to dryness
  4. customtriturated with methanol (20 mL)
  5. filtrationFiltration
  6. customremoved 800 mg of unreacted 4-methoxyoxindole
  7. custompurified by flash chromtography (120 g SiO2, 25% ethyl acetate:hexane to 50% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3e560c4584014bc7b5363b76e7ba51ee
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825220B2

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