Benzylamine → N-[6-[4-(4-Nitrophenyl)butoxy]hexyl]benzenemethanamine

HRID 1721960

Reaktionsgleichung

Reaktionsgleichung von HRID 1721960
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>Cl>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 200714241-(4-((6-Bromohexyl)oxy)butyl)-4-nitrobenzene

Produkt 1

HCID 20029789N-[6-[4-(4-Nitrophenyl)butoxy]hexyl]benzenemethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

1-[4-[(6-Bromohexyl)oxy]butyl]-4-nitrobenzene (8.0 g) was added dropwise to benzylamine (30 ml) at 110°. The solution was heated at 110°-120° for 2 h, treated with hydrochloric acid (2M; 200 ml), and extracted with ethyl acetate (2×150 ml). The organic extract was washed with aqueous sodium carbonate (150 ml) and brine (150 ml), dried and evaporated. The residue was purified by FCC eluting with ether to give the title compound as a pale yellow oil (5.9 g). T.l.c. Ether Rf 0.15.

Aufarbeitung

  1. temperatureThe solution was heated at 110°-120° for 2 h
  2. extractionextracted with ethyl acetate (2×150 ml)
  3. extractionThe organic extract
  4. washwas washed with aqueous sodium carbonate (150 ml) and brine (150 ml)
  5. customdried
  6. customevaporated
  7. customThe residue was purified by FCC
  8. washeluting with ether

Quellen und Nachweise

ORD-Eintrag
ord-b8b288a265c943239010e50fc974339e
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04853381

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