N-Ethyl-N-benzylaniline → N-benzyl-N-(4-bromophenyl)-N-ethylamine

HRID 897497

Reaktionsgleichung

Reaktionsgleichung von HRID 897497
[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]C1C(=O)C(Br)=CC(Br)(Br)C=1>ClCCl>[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7098N-Ethyl-N-benzylanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Produkt 1

HCID 22347350N-benzyl-N-(4-bromophenyl)-N-ethylamineAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-benzyl-N-phenyl-N-ethylamine (2.25 g, 0.0107 mol) was dissolved in anhydrous dichloromethane (80 mL) and 2,4,4,6-tetrabromocyclohexadiene-1-one (4.36 g, 0.0107 mol) was added in 6 equal portions over a 20 min. period. Stirring was continued at ambient temperature for 20 hours; the organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:99) as mobile phase to yield N-benzyl-N-(4-bromophenyl)-N-ethylamine (2.38 g, 0.0082 mol) as a colorless oil.

Aufarbeitung

  1. washthe organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-b0d99dd9e1a740b486e15cd5d2e4a1de
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921763B2

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