N,N-Diethyl-1,3-propanediamine → 3-Diethylaminopropylacetamide

Participants

Reaction Steps

12.60 g (0.09 mol) of N-cyano-N-butylacetamide are refluxed with 13.4 g (0.1035 mol) of diethylaminopropylamine in 25 ml of tetrahydrofuran for 2 hours, after which, according to investigation by gas chromatography, the educt has completely reacted to give 3-diethylaminopropylacetamide, tri-n-butylisomelamine and another component, which probably consists of butyl cyanamide. The mixture is concentrated on a rotary evaporator, and the oil which remains is left to stand at room temperature and the reaction which subsequently takes place is monitored by gas chromatography. After 5 days, the unknown component, which probably consists of butyl cyanamide, has largely reacted and has formed tributylisomelamine by trimerisation. The mixture is distilled in a bulb tube oven, first under 23.4 mbar and at a maximum temperature of 125° C. and then under 0.156 mbar and at a maximum temperature of 180° C. 6 fractions totalling 24.4 g are thereby obtained, analysis of which by gas chromatography gives a yield of 74.7% of tributylisomelamine and 96.7% of 3-diethylaminopropylacetamide. An analysis sample of tributylisomelamine, which is liquid at room temperature, can be isolated by renewed distillation of the fractions obtained under the high vacuum.

Provenance & Evidence