130279-34-4Relevant articles and documents
Electrochemical fluorination of di- and tri-(2-hydroxyethyl)-substituted alkylamines
Abe, Takashi,Soloshonok, Irina,Baba, Hajime,Sekiya, Akira
, p. 51 - 57 (1999)
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.
THE ELECTROCHEMICAL FLUORINATION OF NITROGEN-CONTAINING CARBOXYLIC ACIDS. FLUORINATION OF METHYL ESTERS OF CYCLIC AMINOGROUP SUBSTITUTED CARBOXYLIC ACIDS
Abe, Takashi,Hayashi, Eiji,Fukaya, Haruhiko,Baba, Hajime
, p. 173 - 196 (2007/10/02)
Nine methyl esters of cyclic amino-group substituted carboxylic acids related to glycine, alanine or β-alanine were subjected to electrochemical fluorination.This afforded the corresponding perfluoroacid fluorides together with cleavage products in fair yields.As cyclic amino-substituents, pyrrolidino-, morpholino-, piperidino-, hexamethyleneimino- and N'-methylpiperazinyl-groups were investigated.The formation of cyclized by-products was not observed, which contrasts with the fluorination of aliphatic dialkylamino-substituted carboxylic acids.From such methyl 2-cyclic amino-propionates (cyclic amino-group: a pyrrolidino, a morpholino or a piperidino-group), the perfluorinated methyl esters were obtained together with the corresponding perfluoroacid fluorides in yields of 1-2percent and 14-29percent, respectively.The formation of the former compounds is ascribed to the blocking effect of the bulky cyclic amino-groups.The physical properties of the new compounds obtained are reported together with their spectral (19F NMR, Mass and IR) data.