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Synthesis of deuterium labelled perphenazine
Author(s) -
Hawes E. M.,
Gurnsey T. S.,
Shetty H. U.,
Midha K. K.
Publication year - 1983
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.2580200610
Subject(s) - chemistry , phenothiazine , deuterium , piperazine , lithium (medication) , imide , ring (chemistry) , medicinal chemistry , perphenazine , organic chemistry , medicine , physics , quantum mechanics , pharmacology , endocrinology
Procedures for the preparation of perphenazine‐d 2 , ‐d 4 , and ‐d 6 , and N ‐deshydroxyethylperphenazine‐d 4 and ‐d 6 are described. Deuterium was introduced in the propylpiperazine side chain by treatment of the appropriate ester or imide with lithium aluminum deuteride. The γ‐carbon of the propyl group was labelled with two deuterium atoms by reduction of 2‐chloro‐10‐(2‐methoxycarbonylethyl)‐10 H ‐phenothiazine, while four deuterium atoms were incorporated into the piperazine ring by reduction of 2‐chloro‐10‐[3‐(3,5‐dioxo‐1‐piperazinyl)‐propyl]‐10 H ‐phenothiazine.