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Synthesis of deuterium‐labeled imipramine using acid‐catalyzed exchange reaction
Author(s) -
Baba S.,
Furuta T.,
Sasaki Y.,
Kasuya Y.
Publication year - 1985
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.2580220208
Subject(s) - imipramine , chemistry , deuterium , catalysis , medicinal chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
Synthesis of three forms of selectively deuterated imipramine with high isotopic purity using acid catalyzed hydrogen‐deuterium exchange reaction is described. Deuterated imipramine labeled at the positions of 2,4,6 and 8 [IP‐d 4 (I)] was prepared directly by heating imipramine in 10% DCl‐D 2 O at 80° for 8hr. Imipramine labeled at all of the eight aromatic positions (IP‐d 8 ) was synthesized from iminodibenzyl‐1,2,3,4,6,7,8,9‐d 8 which was prepared by treating iminodibenzyl (IDB) in 37% DCl‐D 2 O at 160° for 24hr. And imipramine labeled at the positions of 1,3,7 and 9 [IP‐d 4 (II)] was obtained by “back‐exchange” of IP‐d 8 under the protio condition according to the exchange procedure of IP‐d 4 (I).