Sodium Hydroxide → 3-Quinuclidinone

HRID 2303931Notes

Reaction equation

HRID 2303931 reaction equation
[OH-].[Na+].Cl.[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C:6](=[O:12])[CH2:5]2>O>[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C:6](=[O:12])[CH2:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 195073-QuinuclidinoneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

99% Sodium hydroxide (97.0 g, 2.4 mol) was dissolved in water (285 ml) and 3-quinuclidinone hydrochloride (193.9 g, 1.2 mol) was added. The mixture was extracted with toluene (600 ml). The obtained aqueous layer was re-extracted with toluene (300 ml). The obtained toluene layer was combined with the toluene layer obtained previously and the mixture was dried over anhydrous magnesium sulfate and concentrated to give a toluene solution (438.1 g) containing 3-quinuclidinone (150.2 g, yield: 100%).

Workup

  1. extractionThe mixture was extracted with toluene (600 ml)
  2. extractionThe obtained aqueous layer was re-extracted with toluene (300 ml)
  3. customobtained previously
  4. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a toluene solution (438.1 g)

Sources & evidence

ORD record
ord-712707dc30ac485a8bbb5edec49a8fcf
Source dataset
uspto-grants-2002_08
Patent number
US06433168B1

Reaction notes

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