Water → 1,4-Diazabicyclo(3.2.2)nonane

HRID 2243816Notes

Reaction equation

HRID 2243816 reaction equation
[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][C:3](=O)[CH2:2]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[N:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[NH:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 962WaterHCID 44018501,4-Diazabicyclo(3.2.2)nonan-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 3984071,4-Diazabicyclo(3.2.2)nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 mom 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 (68%).

Workup

  1. temperaturethe reaction mixture was refluxed for 36 hours
  2. additionwas added dropwise
  3. filtrationthe mixture was filtered
  4. customThe solvent was removed from the filtrate by rotavapor at reduced pressure
  5. distillationThe formed substance was distilled with Kugelrohr (0.5 mBar, 70° C.)

Sources & evidence

ORD record
ord-e3a78983a5654c55a41013a93d058ac2
Source dataset
uspto-grants-2010_03
Patent number
US07678788B2

Reaction notes

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