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

HRID 37834

Reaction equation

HRID 37834 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1>C(O)CCC>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

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

Product 1

HCID 50559501-(4-Nitrophenyl)-1,4-diazepaneYield 42%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A solution of homopiperazine (11.4 g, 114 mmol) in 1-butanol (40 mL) was added to a refluxing solution of 1-chloro-4-nitrobenzene (6.0 g, 38 mmol) in 1-butanol (40 mL) over 15 minutes. The mixture was maintained at reflux for 24 hours then cooled to room temperature and extracted with 2N hydrochloric acid. The aqueous layer was basified with potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 1-(4-nitro-phenyl)-[1,4]diazepane (3.5 g, 42%) as a yellow solid.

Workup

  1. temperatureThe mixture was maintained
  2. temperatureat reflux for 24 hours
  3. extractionextracted with 2N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c60e14d135f433dad7b2bd9ef175647
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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