1-Chloro-4-nitrobenzene → 1-(4-Nitrophenyl)-1,4-diazepane

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Reaction Steps

From 1-chloro-4-nitrobenzene and [1,4]diazepane (homopiperazine) by heating in n-butanol at reflux to give 1-(4-nitro-phenyl)-[1,4]diazepane, followed by reaction with 2-chloro-4,6-dimethylpyridine by heating in the presence of palladium (II) acetate, 2-dicyclohexylphospino-2-(N,N′-dimethyl amino)biphenyl and caesium carbonate in a mixture of toluene and THF to give 1-(4,6-dimethyl-pyridin-2-yl)-4-(4-nitro-phenyl)-[1,4]diazepane, and finally reduction with tin (II) chloride in a mixture of ethanol and ethyl acetate gives the required aniline.

Provenance & Evidence