1,4-Dioxane → 1,4-Diazabicyclo(3.2.2)nonane

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.

1. temperatureThe mixture was refluxed for 6 h
2. customto reach room temperature
3. filtrationfiltered off via glass
4. filtrationfilter
5. customThe solvent was evaporated
6. distillationthe residue was distilled
7. customat 90° C.

ORD record

ord-e46886099daf4b85b96782072bbb84be

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148365B2