Methyl iodide → HCID 22759859, compound

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Reaction Conditions

Reaction Steps

To a solution of 1.46 parts of 2-(2,2-diphenylethyl)-1-azabicyclo[2.2.2]octane in 20 parts by volume of cyclohexane is added under a nitrogen atmosphere 2.4 parts by volume of 2.5 M solution of butyl lithium. The mixture is heated with stirring at reflux temperature for one hour. After cooling this mixture to 0° C. 0.58 part of iodomethane is added. The reaction mixture is then stirred at room temperature for 18 hours. The resulting yellow mixture which contains a white solid and gum is diluted with 100 parts by volume of ethyl ether and then washed with water. The cyclohexane-ethyl ether layer, excluding the gum, is extracted with dilute hydrochloric acid. The acidic, aqueous extract is basified with aqueous sodium hydroxide resulting in the liberation of an oil. This mixture is then extracted with ether. The ethereal extract is dried over anhydrous sodium sulfate and stripped in vacuo to give an oil which is crude 2-(2,2-diphenylpropyl)-1-azabicyclo[2.2.2]octane. This oil is then dissolved in ethyl ether. Treating this ethereal solution with HCl/isoPrOH solution results in the precipitation of a gum. This gum is rinsed with ethyl ether and then dissolved in acetone. The volume of the acetone solution is concentrated and then cooled to induce crystallization. The resulting crystals are filtered, washed with acetone and dried in vacuo to give 2-(2,2-diphenylpropyl)-1-azabicyclo[2.2.2]octane hydrochloride melting at about 261°-264° C. This compound is represented by the following structural formula ##STR9##

Provenance & Evidence