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[ CAS No. 283-38-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 283-38-5
Chemical Structure| 283-38-5
Chemical Structure| 283-38-5
Structure of 283-38-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 283-38-5 ]

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Product Details of [ 283-38-5 ]

CAS No. :283-38-5 MDL No. :MFCD14581694
Formula : C7H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XJKNACDCUAFDHD-UHFFFAOYSA-N
M.W : 126.20 Pubchem ID :398407
Synonyms :

Calculated chemistry of [ 283-38-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.06
TPSA : 15.27 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 0.16
Log Po/w (WLOGP) : -0.71
Log Po/w (MLOGP) : 0.57
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 0.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.72
Solubility : 23.9 mg/ml ; 0.189 mol/l
Class : Very soluble
Log S (Ali) : -0.04
Solubility : 116.0 mg/ml ; 0.916 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.94
Solubility : 14.7 mg/ml ; 0.116 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.9

Safety of [ 283-38-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 283-38-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 283-38-5 ]
  • Downstream synthetic route of [ 283-38-5 ]

[ 283-38-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 53619-11-7 ]
  • [ 283-38-5 ]
YieldReaction ConditionsOperation in experiment
90% With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 6 h; Reflux 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 H20, 200 μ, of 15percent aqueous NaOH, and 600 μ, of H20. The mixture was filtered through Celite which was subsequently washed with EtOAc. The combined filtrate was concentrated in vacuo to afford the product (0.82 g, 90percent) which was used without further purification. XH NMR (400 MHz, CDC13) δ 3.28-3.25 (m, IH), 2.99-2.95 (m, 8H), 1.86-1.80 (m, 3H), 1.69-1.64 (m, 2H) ppm.
90% With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 6 h; Reflux To 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).
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 L of H2O, 200 L of 15percent aqueous NaOH, and 600 L of H2O.
The mixture was filtered through Celite which was subsequently washed with EtOAc.
The combined filtrate was concentrated in vacuo to afford the product (0.82 g, 90percent) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.28-3.25 (m, 1H), 2.99-2.95 (m, 8H), 1.86-1.80 (m, 3H), 1.69-1.64 (m, 2H) ppm.
78% With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 6 h; Heating / reflux 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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. 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
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 <n="16"/>mixture was refluxed for 6 hours 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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. 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 <n="16"/>(0.1 mbar) to yield 1 ,4-diazabicyclo[3.2.2]nonane (1 1 .1 g; 78percent) as colourless hygroscopic material.
78% With lithium aluminium tetrahydride; water In 1,4-dioxane at 20℃; for 6.5 h; Heating / reflux To 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
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) 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 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
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) 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 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.
78% With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux 1 ,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) 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 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃;
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) 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 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃;
,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) 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 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 colorless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃;
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) LiAIH4 (4.9 g; 130 mmol) was added under argon. The mixture was refluxed for 6 hours 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃;
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; 1 13 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. To the reaction mixture water (5 ml in 10 ml of dioxane) was added20 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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) 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 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 colorless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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) 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 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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) 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 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 colorless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
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) 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Inert atmosphere; Reflux
Stage #2: With water In 1,4-dioxane at 20℃; for 0.5 h;
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) 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 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.
78% With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux was 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.
78% With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux 1,4-Diazabicyclo[3.2.2]nonane (Intermediate Compound)
Was prepared according to J. Med. Chem.
1993 36 2311-2320 and the following slightly modified method.
To a 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 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.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
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 20 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; 78percent) as colourless hygroscopic material.
78%
Stage #1: With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux
Stage #2: With water In 1,4-dioxane for 0.5 h;
1 ,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) LiAIH4 (4.9 g; 130 mmol) was added under argon. The mixture was refluxed for 6 hours 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.
78% With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux To the solution of 1 ,4-diazabicyclo[3.2.2]nonan-3-one (15.8 g; 1 13 mmol) in absolute dioxane (130 ml) 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 filtered off via glass filter. The solvent was evaporated and the residue was distilled using Kugelrohr apparatus at 9O0C (0.1 mbar) to yield 1 ,4- diazabicyclo[3.2.2]nonane (1 1 .1 g; 78percent) as colourless hygroscopic material.
78% With lithium aluminium tetrahydride In 1,4-dioxane for 6 h; Heating / reflux 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 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 9O0C (0.1 mbar) to yield 1 ,4- diazabicyclo[3.2.2]nonane (1 1.1 g; 78percent) as colourless hygroscopic material.
68% With lithium aluminium tetrahydride In tetrahydrofuran for 36 h; Heating / reflux 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).
68% With lithium aluminium tetrahydride In tetrahydrofuran for 36 h; Heating / reflux 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).

Reference: [1] Synthetic Communications, 2006, vol. 36, # 3, p. 321 - 326
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[3] Patent: US2004/127491, 2004, A1,
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