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Synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions

✍ Scribed by Naba K. Chaudhuri; Thomas J. Ball

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
252 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

The synthesis of imipramine labelled with four deuterium atoms in 10, 11 positions is described. The intermediate, trideutero‐o‐nitrotoluene was prepared by reduction of o‐nitrobenzoic acid with B~2~D~6~ followed by conversion of the resulting alcohol to the chloride and selective reduction of the chloride with NaBD~4~ in dimethyl sulfoxide. Trideutero‐o‐nitro‐toluene was then converted to tetradeutero‐2,2′‐dinitrodibenzyl by treatment with K‐tert butoxide in presence of air. The dinitro compound was reduced to a diamino compound which was then cyclized by heating its diphosphate salt, and the resulting amine on reaction with 1‐chloro‐3‐dimethylaminopropane gave tetradeuterated imipramine.

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The synthesis of estragole labelled with
The synthesis of estragole labelled with deuterium ln single positions of the allylic side chain. In single positions of the allylic side chain
✍ D. Monti; P. Gramatica; P. Manitto 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 French ⚖ 341 KB

y-2H2]Estragole was synthesized [ methylene-112] -benzyl chloride; [ p-2H] estragole via reduction vinylation of 4-methoxy-2 of 3-(~-anisyl)-propyne with bis-3-methyl-2-butylborane (obtained from LiAl H4 , BF3 etherate and 2-methyl-2-butene) ; k-2H]estragole 2 ? y & cinnamaldehyde with NaBH3CN.