Butylamine → N,N',N''-tri-n-butylcitramide

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Reaction Steps

N,N′,N″-tri-n-butylcitramide was prepared by the reaction of n-butylamine with triethylcitrate. To a round-bottomed flask were added triethylcitrate (31.485 g; 0.1140 mole, 1 eq) and methanol (40 mL). To this solution, n-butylamine (24.999 g; 3.00 eq) was slowly poured. The clear light yellow solution stirred for 3 days at room temperature prior to the removal of methanol via rotary evaporation at 60° C. The resulting crude tacky solid was triturated using diethylether, collected via filtration and dried in vacuo to give a white powder with a slight amine odor (23.95 g; 58% yield).

Provenance & Evidence