3-Quinuclidinone, hydrochloride

Quinuclidinone hydrochloride (0.49 mol) was treated with potassium hydroxide (0.54 mol) dissolved in 420 ml methyl alcohol and then stirred 30 minutes at ambient temperature. 3-Pyridine-carboxaldehyde (0.54 mol) was then added and the mixture stirred for an additional 16 hours. Solid cakes, which formed on the flask walls, were broken up and dissolved with the addition of 390 ml rapidly stirring water. The mixture was kept cooled to 4°C overnight and a precipitate formed, which were collected by filtration. These crystals were then washed with water, air dried, and 80 g product isolated as yellow solid. A second product crop of 8 g was obtained by reducing the filtrate volume by 90%, so a total product yield of 82% was observed. 

Azabicyclo(2.2.2)octan-3-one, hydrochloride EINECS 214-776-5 NSC 91498 Quinuclidin-3-one hydro-chloride 3-Quinuclidinone hydrochloride. Janssen Chimica Lancaster Synthesis Co. 

Methoxyquinoline-4-carboxaldehyde and 3-quinuclidinone hydrochloride added to a soln. of Na in abs. ethanol, warmed to 35°, swirled ca. 5 min., and allowed to stand 2 hrs. at room temp. -> 6 -methoxy-7-oxo-8-rubene. Y 91%. - Of the two possible geometrical isomers, only that with the ketone function trans to the quinoline ring is formed. D. R. Bender and D. L. Coffen, J. Org. Chem. 33, 2504 (1968). 

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