4-[2-(3-nitrophenoxy)ethyl]morpholine → 3-(2-Morpholin-4-ylethoxy)aniline

HRID 448396

Reaktionsgleichung

Reaktionsgleichung von HRID 448396
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[O:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[N:10]1([CH2:9][CH2:8][O:7][C:6]2[CH:5]=[C:4]([NH2:1])[CH:18]=[CH:17][CH:16]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Komponenten

5

Edukt 2

HCID 29960364-[2-(3-nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 64866163-(2-Morpholin-4-ylethoxy)anilineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-[2-(3-nitro-phenoxy)-ethyl]-morpholine (4.0 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (100 mL) was hydrogenated under 50 psi hydrogen for 23 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 3.0 g, in 86% yield; 1H NMR (CDCl3) δ 2.58 (t, J=4.7 Hz, 4H), 2.78 (t, J=5.8 Hz, 2H), 3.65 (br, 2H), 3.73 (t, J=4.7 Hz, 4H), 4.07 (t, J=5.8 Hz, 2H), 6.24-6.34 (m, 3H), 7.05 (t, J=8.1 Hz, 1H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customproviding 3.0 g

Quellen und Nachweise

ORD-Eintrag
ord-a4f549bad89d4d25baf31ac812062696
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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