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Synthese d'un Antagoniste Alpha Adrenergique Marque au Tritium: WB 4101 [benzodioxanyl‐1,4‐ 3 H‐2,3], ou N‐[dimethoxy‐2,6 phenoxyethyl] aminomethyl‐2 benzodioxanne‐1,4[ 3 H‐2,3]
Author(s) -
Guillaumet G.,
Coudert G.,
Ponchant M.,
Beaucourt J. P.,
Pichat L.
Publication year - 1984
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.2580210209
Subject(s) - chemistry , medicinal chemistry , tritium , catalysis , benzene , sodium iodide , catechol , acetone , iodide , nuclear chemistry , organic chemistry , nuclear physics , physics
The synthesis of an alpha adrenergic antagonist labelled with tritium: [(2,3‐ 3 H)‐1,4‐benzodioxanye] WB 4101 or 2‐N[2,6 dimethoxyphenoxyethye] aminomethyl 2,3‐ 3 H‐1,4 benzodioxan is described. 2‐cyano‐1,4‐benzodioxan: 1 was prepared from catechol and 2‐chloroacrylonitrille and then converted to 2‐cyano‐1,4‐benzodioxin: 2 by the successive actions of N‐bromosuccinimide in CCl 4 and sodium iodide in acetone. 2 was reduced with lithium aluminium hydride into 2‐aminomethyl‐1,4‐benzodioxin: 3 and then converted to 2‐[N‐(2,6‐dimethoxyphenoxyethyl)‐aminomethyl]‐1,4‐benzodioxin: 4a , and its hydrochloride: 4b . The catalytic reduction of 4a , 4b with tritium in various and in presence of various catalysts was studied. The best result was obtained with Wilkinson's catalyst in benzene giving rise to [(2,3‐ 3 H)1,4‐benzodioxanyl]WB 4101 with a specific activity of 60 CilmMole. 3 H.NMR and MS analyses are also described.