Dimethylamine → N-(2-Methoxyphenyl)-4-dimethylaminomethylbenzamide

HRID 2454

Reaktionsgleichung

Reaktionsgleichung von HRID 2454
Cl[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:8])=[CH:5][CH:4]=1.[CH3:20][NH:21][CH3:22]>O1CCOCC1>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([CH2:2][N:21]([CH3:22])[CH3:20])=[CH:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamide

Produkt 1

HCID 19690030N-(2-Methoxyphenyl)-4-dimethylaminomethylbenzamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

In an atmosphere of argon, 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) was put into a 25 ml capacity eggplant type flask equipped with a cold finger and dissolved in dioxane (3 ml), followed by the addition of 50% dimethylamine aqueous solution (3 ml) at room temperature. After 2.5 hours of stirring at 80° C. and subsequent removal of dioxane by evaporation, the resulting residue was diluted with ethyl acetate (30 ml). The thus diluted solution was dried on anhydrous sodium carbonate, and the resulting residue was purified by subjecting it to a silica gel column chromatography (ether-ethyl acetate-ethyl acetate:methanol=10:1) to obtain 284 mg (100%) of the title compound in the form of colorless oil.

Aufarbeitung

  1. customequipped with a cold finger
  2. customsubsequent removal of dioxane
  3. customby evaporation
  4. additionthe resulting residue was diluted with ethyl acetate (30 ml)
  5. dry with materialThe thus diluted solution was dried on anhydrous sodium carbonate
  6. customthe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-e6f09e6358c645c8a45e3f4af446ce3d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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