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Synthesis of 7-chloro-1,3,-dihydro-3-hydroxy-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one-2-14c (2-14C-temazepam)

✍ Scribed by Jeremy G. Dain

Publisher
John Wiley and Sons
Year
1987
Tongue
French
Weight
217 KB
Volume
24
Category
Article
ISSN
0022-2135

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✦ Synopsis

Tema~epam-2-'~C, 7-Chloro-1,3-ihydro-3-hydroxy-1 -methyl-5-phenyl-2H-1,4-benzodiazepin-2-one--"C, was prepared in a f ive-step synthesis. Chl~roacetic-l-~~C acid was converted to the acid chloride with thionyl chloride. The acid chloride was allowed to react with 2-methylamino-5-chloro-benzophenone to form the amide.

The amide was reacted with hydroxylamine and directly cyclized to the benzodiazepine N-oxide which was converted to the acetate with acetic anhydride. sulfuric acid to give the final product (3.8% radiochemical yield at 52. mCi/mol).

This procedure provides temazepam with the radiolabel in a metabolically stable position.

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