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 hours and then allowed to reach room temperature. Water (5 ml in 10 ml of dioxane) was added by drops to the reaction mixture, 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 hours
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-29e94cad386d4133a10b11f77c80e686

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220741B2