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

HRID 4978

Reaction equation

HRID 4978 reaction equation
[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

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 195073-Quinuclidinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-247ca74c98124c71aa0d4daf168eb8af
Source dataset
uspto-grants-1993_09
Patent number
US05242930

Linked notes

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