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

HRID 37834

Reaktionsgleichung

Reaktionsgleichung von HRID 37834
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4c60e14d135f433dad7b2bd9ef175647
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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