1,4-Diazobicylco[3.2.2]nonane

To a stirred solution of l, 4-diazabicyclo[3.2.2]nonan-3-one (1.0 g, 7.2 mmol) in 1, 4-dioxane (7.2 mL) at room temperature was added lithium aluminum hydride [2.0M/THF] (4.1 mL, 8.2 mmol). The reaction mixture was then heated at reflux for 6 hours before cooling to room temperature. The reaction was quenched by the stepwise addition of 200 μ, of HTo a stirred solution of 1, 4-diazabicyclo[3.2.2]nonan-3-one (1.0 g, 7.2 mmol) in 1, 4-dioxane (7.2 mL) at room temperature was added lithium aluminum hydride [2.0M/THF] (4.1 mL, 8.2 mmol). To the solution of 1, 4-diazabicyclo [3.2. 2] nonan-3-one (15.8 g ; 113 mmol) in absolute dioxane (130 mi) LiAIH4 (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 tittered 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; 78percent) as colourless hygroscopic material.To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIHTo a solution of 1, 4-DIAZABICYCLO [3.2. 2] nonan-3-one (15.8 g, 113 MMOL) in absolute dioxane (130 ML), LiAIH4 (4.9 g, 130 MMOL) was added under argon. The mixture was refluxed for 6 hours and then allowed to reach room temperatre. To this 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 a Kugelrohr apparatus at 90°C (0.1 mbar) to yield 1, 4-DIAZABICYCLO [3. 2.2] nonane (11.1 g, 78percent) as colourless hygroscopic material.1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound) To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound) To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicyclo[3.2.21nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH, 4-Diazabicyclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicyclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicvclo[3.2.2]nonane (Intermediate compound); To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1, 4-Diazabicvclo[3.2.21nonane (Intermediate compound). To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) LiAIH (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 (1 1 .1 g; 78percent) as colourless hygroscopic material.1 , 4-Diazabicvclo[3.2.21nonane (Intermediate compound)To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) LiAIHwas prepared according to J. Med. Chem. 1993 36 2311-2320, and according to the following slightly modified method. To the solution of 1, [4-DIAZABICYCLO] [3.2. 2] nonan-3-one (15.8 g, 113 [MMOL)] in absolute dioxane (130 ml) LiAIH4 (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, 78percent) as colourless hygroscopic material.1, 4-Diazabicyclo[3.2.2]nonane (Intermediate Compound) To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1 , 4-Diazabicyclor3.2.2lnonane (Intermediate compound)To the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) LiAIHTo the solution of 1 , 4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 113 mmol) in absolute dioxane (130 ml) LiAIH1, 4-DIAZABICYCLO [3.2. 2] NONAN-3-ONE (5.12 G ; 36 MMOL) was dissolved in tetrahydrofuran (50 ML), litium aluminium hydride 2.28 G (60 MMOL) was added to the solution and the reaction mixture was refluxed for 36 hours. After cooling the reaction mixture to room temperature, water (2.3 ml) was added dropwise and the mixture was filtered. The solvent was removed from the filtrate by rotavapor at reduced pressure. The formed substance was distilled with Kugelrohr (0.5 MBAR, 70 C). Yield of the title compound 3.11 G (68percent).1. 4-Diazabicyclor3. 2. 21nonane fJ. Med. Chem. 1993 36 2311-23201 (Intermediate compound); 1, 4-Diazabicyclo [3.2. 2] nonan-3-one (5.12 g ; 36 mmol) was dissolved in tetrahydrofuran (50 ml), litium aluminium hydride 2. 28 g (60 mmol) was added to the solution and the reaction mixture was refluxed for 36 hours. After cooling the reaction mixture to room temperature, water (2.3 ml) was added dropwise and the mixture was filtered. The solvent was removed from the filtrate by rotavapor at reduced pressure. The formed substance was distilled with Kugelrohr (0.5 mBar ; 70°C). Yield of the title compound 3.11 g (68percent).

Molecular Weight:126.20
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:126.115698455
Monoisotopic Mass:126.115698455
Topological Polar Surface Area:15.3
Heavy Atom Count:9
Complexity:95.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes