Electrochemical Fluorination of Di- and Tri-(2-hydroxyethyl)-substituted Alkylamines.

Abstract Several 2-(hydroxyethyl)-substituted alkylamines like 1,4-bis(2-hydroxyethyl)piperazine, N , N -bis(2-hydroxyethyl)methylamine, N , N -bis(2-hydroxyethyl)ethylamine, and N , N , N -tris(2-hydroxyethyl)amine as well as their derivatives (HCl salts, a borate and trimethylsilylethers) were subjected to electrochemical fluorination. From 1,4-bis(2-hydroxyethyl)piperazine, F -[1,4-bis(fluorocarbonylmethyl)piperazine] was obtained in low yield. In the fluorination of N , N -bis(2-hydroxyethyl)alkylamines and N , N , N -tris(2-hydroxyethyl)amine, cyclization occurred extensively, affording large quantities of F -morpholine derivatives. However, F - N , N -bis(fluorocarbonylmethyl)methylamine was obtained from the former in low, isolated yield.