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Water → N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amine

HRID 1007890
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1007890
[OH-].[Na+].[C:3]1([CH2:13][CH2:14][OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl.Cl[CH2:18][CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22].O>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:19]([N:20]([CH2:23][CH3:24])[CH2:21][CH2:22][O:15][CH2:14][CH2:13][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 13047Naphthalen-1-ethanolHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14798Sodium Hydroxide

Produkt 1

HCID 22666300N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amineAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433
Tetrabutylammonium hydrogen sulfate
Katalysator
HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

In a mixture of 1 mL of toluene and 3.5 ml of 50% (W/V) aqueous solution of sodium hydroxide is suspended 0.70 g of 2-(1-naphthyl)-1-ethanol, to which are added 1.00 g of N-(2-chloroethyl)-N,N-diethylamine hydrochloride and 0.14 g of tetra-n-butylammonium hydrogen sulfate. The mixture is heated under reflux for 2.5 hours. Water and toluene are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent:chloroform:methanol=10:1). Thus, 1.06 g of N,N-diethyl-N-{2-[2-(1-naphthyl)ethoxy]ethyl}-amine is obtained as an oily product.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2.5 hours
  3. customthe organic layer is separated
  4. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography (eluent:chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-2fe18f332ad74cbe881d18eae9764afc
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06797726B1

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