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Synthesis of 3‐Chloro‐2‐hydroxyimipramine and 3‐chloro‐8‐hydroxyimipramine , Hypothetical metabolites of clomipramin
Author(s) -
Zirnis Aija,
Piszkiewicz Frederick F.,
Martian Albert A.
Publication year - 1976
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570130213
Subject(s) - chemistry , dihydropyran , biotransformation , salt (chemistry) , organic chemistry , stereochemistry , catalysis , enzyme
Abstract Fremy salt oxidation of 3‐chloroiminodibenzyl yields a mixture of two isomeric iminequinones, which can be separated and reduced to aminophenols and the phenolic group protected with addition of dihydropyran. Introduction of the N,N ‐dimethylaminopropyl side chain and removal of the protective group provided the two chlorohydroxyimipramines, which can serve as standards for the identification of possible biotransformation products of the parent drug, clomipramine.