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Synthesis of deuterium‐labelled viloxazine
Author(s) -
Mamada Kumiko,
Furuta Takashi,
Kasuya Yasuji
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580250611
Subject(s) - chemistry , epoxide , morpholine , deuterium , epichlorohydrin , ethyl iodide , derivative (finance) , alkylation , organic chemistry , medicinal chemistry , catalysis , physics , quantum mechanics , financial economics , economics
The synthesis of deuterium‐labelled viloxazine with high isotopic purity is described. The synthetic procedures employ alkylation of 2‐(benzyloxy)phenol with [ 2 H 5 ]ethyl iodide for the introduction of deuterium. Catalytic removal of the benzyl group of the deuterated product followed by reaction with epichlorohydrin afforded 1,2‐epoxy‐3‐(2′‐pentadeuteroethoxyphenoxy)propane. Addition of 2‐aminoethyl hydrogen sulphate to the epoxide and subsequent ring formation into a morpholine derivative produced the desired [ 2 H 5 ] viloxazine.