Kinetic studies of the reactions of 2‐diethylaminoethylchloride with nucleophilic reagents in N,N‐dimethylformamide

The kinetics of the reactions of 2‐diethylaminoethylchloride with nucleophilic reagents have been studied in N, N‐dimethylformamide from 33 to 80°. An ethyleneimmonium ion is easily formed from 2‐diethylaminoethylchloride by the participation of the neighbouring nitrogen atom. This ion is rather stable in N, N‐dimethylformamide solution and is in equilibrium with 2‐diethylaminoethylchloride. However, it reacts very rapidly with various nucleophilic reagents such as 8‐benzyltheophylline and 2‐(ethylamino)ethanol. The formation of the ethyleneimmonium ion is slower than the nucleophilic substitution reaction. The equilibrium constant and the rate constant of the formation of the ethyleneimmonium ion, as well as the rate constants of the nucleophilic substitution reactions, have been determined.