Electrochemical fluorination of di- and tri-(2-hydroxyethyl)-substituted alkylamines

Add time:07/24/2019    Source:sciencedirect.com

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.

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