Dodecanohydrazide → 1-[N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamoyl]2-dodecanoylhydrazine

Participants

Reaction Steps

Into a 3-necked 300 ml flask was introduced a 60.9% solution of ethyl N-(2,2,6,6-tetramethyl-4-piperidinyl)oxamate in methanol (21.0 g, 0.05 mole), lauric acid hydrazide (13.5 g) and 150 ml of anhydrous methanol. The flask was equipped with a thermometer, a magnetic stirrer and a Dean Stark trap with a reflux condenser. The reaction mixture was heated to reflux and the methanol was slowly distilled off through the Dean Stark trap. The disappearance of the starting materials and the formation of the products were monitored by liquid chromatography. After 6 hours at reflux and the removal of 110 ml of methanol, the liquid chromatograph scans indicated the reaction was essentially complete. The reaction mixture was filtered hot and the filtrate was stripped to dryness on a rotating evaporator under reduced pressure. The residue was a white powder weighing 16.6 g and had a melting range of 80°-84° C. An infrared scan (nujol mull) of the product contained strong carbonyl bands at 1655, 1580 and 1490 cm-1.

Provenance & Evidence