1-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1) → 3-Quinuclidinone

HRID 1824725Notes

Reaction equation

HRID 1824725 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2>C([O-])(O)=O.[Na+]>[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2

Participants

3

Reactant 1

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

Product 1

HCID 195073-QuinuclidinoneYield 88%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

3-Quinuclidinone hydrochloride (Aldrich, 16.1 g, 100 mol) was treated with saturated with NaHCO3 (20 mL) at ambient temperature for 10 minutes. It was then extracted with diethyl ether (4×100 mL). The extracts were combined, washed with brine (2×20 mL) and dried over MgSO4 (Aldrich, anhydrous). The drying reagents were removed by filtration and the filtrate was concentrated under reduced pressure at ambient temperature to give the title compound as white solid (11.0 g, 88% yield). MS (DCl/NH3) m/z 126 (M+H)+.

Workup

  1. extractionIt was then extracted with diethyl ether (4×100 mL)
  2. washwashed with brine (2×20 mL)
  3. dry with materialdried over MgSO4 (Aldrich, anhydrous)
  4. customThe drying reagents were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure at ambient temperature

Sources & evidence

ORD record
ord-1035ebf159c841f3846f9e565532797d
Source dataset
uspto-grants-2006_05
Patent number
US07045530B2

Reaction notes

Loading…