Dimethylformamide → 1-[3,5-Dimethoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl)ethanone

HRID 497032

Reaktionsgleichung

Reaktionsgleichung von HRID 497032
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:11][O:10][C:7]1[CH:6]=[C:5]([C:12](=[O:14])[CH3:13])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 17198AcetosyringoneHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Produkt 1

HCID 223181171-[3,5-Dimethoxy-4-(2-morpholin-4-yl-ethoxy)-phenyl)ethanoneAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In a vial, 500 mg (2.5 mmol) of 3′,5′-dimethoxy-4′-hydroxyacetophenone was combined with 4-(2-chloroethyl)morpholine hydrochloride (600 mg, 3.2 mmol), and powdered potassium carbonate (1.5 g, excess). Dimethylformamide (2 mL) was added, the vial was sealed, and the rxn was heated to 80° C. overnight. The reaction was diluted with water and extracted with diethyl ether. The organic extract was washed with brine, dried (Na2SO4), and evaporated in vacuo to afford 540 mg (67%) of 14 as a white solid.

Aufarbeitung

  1. customthe vial was sealed
  2. extractionextracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-25d2e860e6bc4b9cb622bc039d6f7343
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949544B2

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