Reaction #632019

Reaction equation

1,4-diazabicyclo[3.2.2]nonan-3-one

dioxane

→

1,4-diazabicyclo[3.2.2]nonane

Yield 78.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed for 6 h
2. 2
   Otherto reach room temperature
3. 3
   Filtrationfiltered off via glass
4. 4
   Filtrationfilter
5. 5
   OtherThe solvent was evaporated
6. 6
   workup.DISTILLATIONthe residue was distilled
7. 7
   Otherat 90° C.

Procedure

To the solution of 1,4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAlH4 (4.9 g; 130 mmol) was added under argon. The mixture was refluxed for 6 h and then allowed to reach room temperature. To the reaction mixture water (5 ml in 10 ml of dioxane) was added by drops, the mixture was stirred for 0.5 hour and then filtered off via glass filter. The solvent was evaporated and the residue was distilled using Kugelrohr apparatus at 90° C. (0.1 mbar) to yield 1,4-diazabicyclo[3.2.2]nonane (11.1 g; 78%) as colourless hygroscopic material.

Source