Reaction #632027

Reaction equation

3-quinuclidinone

benzaldehyde

sodium hydroxide

→

(Z)-2-benzylidenequinuclidin-3-one

Yield 91.2%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas refluxed for 1.5 h
2. 2
   TemperatureAfter the solution was cooled
3. 3
   Otherthe yellow precipitates
4. 4
   Otherwere collected
5. 5
   Washwashed with ethanol
6. 6
   Otherdried

Procedure

A mixture of 3-quinuclidinone (20.9 g, 167 mmol), benzaldehyde (17.7 g, 167 mmol), and one pellet of sodium hydroxide in 75 mL of ethanol was refluxed for 1.5 h. After the solution was cooled, the yellow precipitates were collected, washed with ethanol, and dried to give (Z)-2-benzylidenequinuclidin-3-one (32.5 g, yield: 91.2%, mp 130-132° C.).

Source