HCID 22902101, compound → 1,5-Diazabicyclo(3.2.2)nonane

HRID 1489518Notes

Reaction equation

HRID 1489518 reaction equation
O=[C:2]1[N:7]2[CH2:8][CH2:9][CH2:10][N:4]([CH2:5][CH2:6]2)[CH2:3]1>[OH-].[K+]>[N:4]12[CH2:10][CH2:9][CH2:8][N:7]([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

3

Reactant 1

HCID 22902101HCID 22902101, compound

Product 1

HCID 1361141,5-Diazabicyclo(3.2.2)nonane

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

The title compound of Example 2 (1.70 g, 12.1 mmol) was added portionwise at room temperature to a stirred solution of AIH3 (60 mL of a 1.0M solution, 60 mmol). The solution became warm. Stirring was continued for a further 20 minutes and the reaction mixture was poured into cold (5° C.) 30% aqueous KOH solution (100 mL) and the aqueous mixture was extracted with CHCl3 (200 mL). The organic extract was dried (Na2SO4) and evaporated to give the title compound in quantitative yield: mp 250° C. (dec) (EtOH); 1H-NMR (CDCl3) δ 3.02-3.25 (m, 1H), 2.66-3.02 (complex m, 3H), 2.59 (m, 1H), 2.43 (m, 1H), 2.25-2.40 (m, 1H), 1.87 (m, 1H), 1.04-1.77 (complex m, 6H); Anal (calcd for C17H16Cl2N2 ·0.33H2O): C 40.99, H 8.19, N 13.66. Found C 41.00, H 8.31, N 13.68.

Workup

  1. temperatureThe solution became warm
  2. extractionthe aqueous mixture was extracted with CHCl3 (200 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3e1e3452a4eb43cfb53bc36405485b41
Source dataset
uspto-grants-1997_10
Patent number
US05679673

Reaction notes

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