Reacción #5074

Ecuación de reacción

1-Azabicyclo[2.2.2]octan-3-one

2-chlorobenzaldehyde

potassium hydroxide

→

title compound

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe volatiles were removed in vacuo
2. 2
   Lavadothe residue washed with sodium hydrogen carbonate
3. 3
   ExtracciónThis was extracted (×4) with dichloromethane
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried (MgSO4)
6. 6
   OtroThe dichloromethane was removed in vacuo
7. 7
   Otrothe residue recrystallised from methanol-dichloromethane

Procedimiento

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:

Fuente