Michael Addition Reaction of Amines in the Presence of 4-(N,N-Dimethylamino)pyridinium Acetate

In this research, first in a sample aza-Michael addition reaction, the catalytic activity of some protic ionic liquids was investigated. The results show that 4-(N,N-dimethylamino)pyridinium acetate had a superior catalytic activity. Then, Michael's addition reaction of different amines with Michael acceptors including n-butyl acrylate, acrylonitrile, and methyl vinyl ketone in the presence of 4-(N,N-dimethylamino)pyridinium acetate under solvent-free conditions at 100 ºC was studied. The reaction of aromatic and aliphatic primary amines with n-butyl acrylate and acrylonitrile was successful and only mono N-alkylated product was obtained. The reaction of morpholine as a secondary aliphatic amine with three Michael acceptors including n-butyl acrylate, acrylonitrile, and methyl vinyl ketone was accomplished very fast.