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

HRID 880412Notes

Reaction equation

HRID 880412 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C(O)CCC>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 74741-Chloro-4-nitrobenzeneHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 50559501-(4-Nitrophenyl)-1,4-diazepane

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-1a2e304be8bd492096e43100b22ec24d
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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