4-[2-(4-Nitrophenoxy)ethyl]morpholine → 4-(2-Morpholinoethoxy)aniline

HRID 448393

Reaktionsgleichung

Reaktionsgleichung von HRID 448393
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:17]=[CH:18][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Komponenten

5

Edukt 2

HCID 8008814-[2-(4-Nitrophenoxy)ethyl]morpholineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 64847114-(2-Morpholinoethoxy)anilineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-[2-(4-nitro-phenoxy)-ethyl]-morpholine (3.2 g, 13 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 mL) was hydrogenated under 50 psi hydrogen for 20 hours. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo, providing 2.0 g, in 72% yield; 1H NMR (CDCl3) δ 2.57 (t, J=4.6 Hz, 4H), 2.77 (t, J=5.8 Hz, 2H), 3.74 (t, J=4.6 Hz, 4H), 4.04 (t, J=5.8 Hz, 2H), 6.63 (d, J=8.8 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H).

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated in vacuo
  3. customproviding 2.0 g

Quellen und Nachweise

ORD-Eintrag
ord-2fca45d249b74f8dbbc330c160847dcc
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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