Ammonia → HCID 21447123, compound

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Reaction Steps

To a solution of 25 parts by volume liquid ammonia in 22 parts dry tetrahydrofuran is added dropwise over a 5 minute period 10 parts by volume of a 2.3 M solution of butyl lithium in hexane under reflux under a dry ice condenser. Then, a solution of 3.9 parts methyl 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionate in 18 parts dry tetrahydrofuran is added dropwise, with stirring. After stirring the resulting mixture under reflux for 3 hours the dry ice condenser is removed, and the mixture stirred at ambient temperature for a further two hours. The solvents are then removed in vacuo. The residual gum is suspended in water and extracted with a 1:1 ether-benzene solution. The ether-benzene extract is separated, washed with water, dried over anhydrous sodium sulfate and stripped in vacuo. The residue is triturated with 50 parts of n-pentane. The undissolved solid is filtered off, washed with n-pentane and air dried to give a white powder. This powder is recrystallized from a mixture of benzene and petroleum ether to afford, as white needles, 2,2-diphenyl-3-(1-azabicyclo[2.2.2]oct-2-yl)propionamide. This compound melts at about 192°-194° C. and is represented by the following structural formula. ##STR12##

Provenance & Evidence