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The synthesis of 7-chloro-5-pentadeuteriophenyl-1-methyl-1h-1,5-benzodiazepine-2,4(3H, 5H)dione ([2H5]clobazam)

✍ Scribed by Anthony G. Borel; Frank S. Abbott

Publisher: John Wiley and Sons
Year: 1990
Tongue: French
Weight: 452 KB
Volume: 28
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580280706

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✦ Synopsis

Abstract

Pentadeuteriophenyl clobazam 5 was synthesized in essentially quantitative isotopic purity, and characterized by ^1^H‐NMR and mass spectroscopy. The title compound was found to be ≥98% pure by HPLC, and its retention time (t~R~ 6.17 min) was less than that of an authentic clobazam standard (t~R~ 6.32 min). Of the five steps in the synthesis of 5, the most susceptible to deuterium exchange was the nucleophilic substitution of 2,4‐dichloronitrobenzene by aniline‐d~7~ to form N‐(5‐chloro‐2‐nitrophenyl)pentadeuteriophenylamine 2. In this step, the isotopic impurity aniline‐2,3,4,5,‐d~5~ introduced protons from nitrogen into the ortho and para positions of the deuteriophenyl ring of 2.

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