Allyl bromide → 2-(2,2-Diphenyl-4-penten-1-yl)-1-azabicyclo[2.2.2]octane

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Reaction Steps

To a solution of 2.91 parts of 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octane in 40 parts by volume of cyclohexane are added under a nitrogen atmosphere 4.6 parts by volume of a 2.5 M solution of butyl lithium in hexane and 1.5 parts by volume of N,N,N'N'-tetramethylethylenediamine. The mixture is heated to reflux, with stirring, for 12/3 hour and then cooled to room temperature. 1.45 Parts of 3-bromopropene is then added during a 5-second period. Stirring is continued for about 6 minutes during which time the internal temperature reaches a maximum of 43° C. and then subsides. The resulting yellow mixture is washed with seven portions of water and then extracted with dilute hydrochloride acid. The acidic, aqueous extract is washed with ethyl ether and then basefied with aqueous sodium hydroxide resulting in the liberation of an oil. This oil is then extracted with ethyl ether. The ethereal extract is dried over anhydrous sodium sulfate and stripped in vacuo to give a light brown oil. This oil is crystallized from methanol and water to afford as a white solid, 2-(2,2-diphenyl-4-pentenyl)-1-azabicyclo[2.2.2]octane melting at about 95.5°-98° C. This compound is represented by the following structural formula: ##STR7##

Provenance & Evidence