2-Chlorobenzaldehyde → 2-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one

HRID 4978

Reaktionsgleichung

Reaktionsgleichung von HRID 4978
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[CH2:2]2.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O.[OH-].[K+]>CO>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[C:2]1[C:3](=[O:9])[CH:4]2[CH2:7][CH2:8][N:1]1[CH2:6][CH2:5]2

Komponenten

5

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 195073-Quinuclidinone

Produkt 1

HCID 2974052-(2-Chlorobenzylidene)-1-azabicyclo[2.2.2]octan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-Azabicyclo[2.2.2]octan-3-one (3.86 g) was heated at reflux with 2-chlorobenzaldehyde (8.33 ml), potassium hydroxide (0.4 g) and methanol (60 ml) under nitrogen for 2.5 hours. The volatiles were removed in vacuo and the residue washed with sodium hydrogen carbonate. This was extracted (×4) with dichloromethane. The organic layer was washed with water and dried (MgSO4). The dichloromethane was removed in vacuo and the residue recrystallised from methanol-dichloromethane, to afford the title compound as yellow crystals:

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. washthe residue washed with sodium hydrogen carbonate
  3. extractionThis was extracted (×4) with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe dichloromethane was removed in vacuo
  7. customthe residue recrystallised from methanol-dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-247ca74c98124c71aa0d4daf168eb8af
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242930

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