(4-Nitrophenyl)acetic acid → 1-(4-Morpholinyl)-2-(4-nitrophenyl)ethanone

HRID 1744386

Reaktionsgleichung

Reaktionsgleichung von HRID 1744386
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+]>O1CCCC1>[N:14]1([C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Komponenten

5

Edukt 3

HCID 4661(4-Nitrophenyl)acetic acidHCID 8083MorpholineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 51701651-(4-Morpholinyl)-2-(4-nitrophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

A room temperature solution of 1.8839 gms. (4-Nitro-phenyl)-acetic acid in tetrahydrofuran (5 mL) is treated with 1.8069 gms. 1′,1′-carbonyl-diimidizole. The reaction mixture is stirred for 1 h. The reaction mixture is then treated with 1.0 mL morpholine. The reaction is heated overnight at 35° C. The reaction is then allowed to cool to room temperature, and is made basic with the addition of saturated aqueous sodium bicarbonate. The resulting mixture is extracted with ethyl acetate. The aqueous layer is re-extracted four more times with ethyl acetate. The combined organics are evaporated to dryness in vacuo. The crude product residue is then chromatographed by flash silica gel chromatography using 60% ethyl acetate in hexanes as the eluant. Following evaporation of solvent, 1-morpholin-4-yl-2-(4-nitro-phenyl)-ethanone is isolated as a white solid in the amount of 1.4009 gms.

Aufarbeitung

  1. customA room temperature solution of 1.8839 gms
  2. temperatureto cool to room temperature
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. extractionThe aqueous layer is re-extracted four more times with ethyl acetate
  5. customThe combined organics are evaporated to dryness in vacuo
  6. customThe crude product residue is then chromatographed by flash silica gel chromatography
  7. customevaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-07f677bb7b564972bb98ff7a49dfa6c8
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015220B2

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