Bis(2-chloroethyl) ether → 4-(3-Methoxyphenyl)morpholine

HRID 884429

Reaktionsgleichung

Reaktionsgleichung von HRID 884429
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.Cl[CH2:11][CH2:12][O:13][CH2:14][CH2:15]Cl.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 8115Bis(2-chloroethyl) etherHCID 108243-MethoxyanilineHCID 81531Diisopropylethylamine

Produkt 1

HCID 99643354-(3-Methoxyphenyl)morpholineAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of m-anisidine (11.2 mL, 0.1 mol), chloroethyl ether (11.7 mL, 0.1 mol), and diisopropylethylamine (35 mL, 0.2 mol) in toluene (100 mL) was stirred at reflux for 72 h. The precipitate was removed by filtration and washed with toluene (100 mL). The combined toluene solutions were concentrated in vacuo and purified by distillation (120-130° C., 0.2 Torr) to afford the intermediate 4-(3-methoxyphenyl)-morpholine (14.9 g, 77%).

Aufarbeitung

  1. temperatureat reflux for 72 h
  2. customThe precipitate was removed by filtration
  3. washwashed with toluene (100 mL)
  4. concentrationThe combined toluene solutions were concentrated in vacuo
  5. distillationpurified by distillation (120-130° C., 0.2 Torr)

Quellen und Nachweise

ORD-Eintrag
ord-734dd9a18be44d608faa48acba7c156f
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242115B2

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