Triethylamine → (E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamide

HRID 428139

Reaktionsgleichung

Reaktionsgleichung von HRID 428139
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:9]=1.C(Cl)(=O)C(C)(C)C.Br.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:37](=[O:41])[CH2:38][NH:39][CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]>ClCCl>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([C:37](=[O:41])[CH2:38][N:39]([CH3:40])[C:16](=[O:18])/[CH:15]=[CH:14]/[C:10]2[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=2)[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 62493Pivaloyl chlorideHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 183578301-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide

Produkt 1

HCID 20701373(E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamideAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dichloromethane (50 ml) and triethylamine (2.69 ml, 19.30 mmol) were sequentially added to trans-3-(3-pyridyl)acrylic acid (1.44 g, 9.65 mmol) and stirred for 10 minutes. Then, pivaloyl chloride (1.18 ml, 9.65 mmol) was added and stirred for 13 minutes. 1-(3,4-Dimethoxyphenyl)-2-(methylamino)ethanone hydrobromide (2.79 g, 9.65 mmol) was dissolved in dichloromethane (4 ml) and triethylamine (1.34 ml, 9.65 mmol), added to the reaction mixture and stirred at room temperature for 30 minutes. After the reaction mixture was washed with water and aqueous saturated sodium bicarbonate solution, the organic phase was dried over magnesium sulfate and the solvent was distilled out under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1) to yield a crude product. The crude product was recrystallized to yield the titled compound (1.84 g, 5.41 mmol, 56%).

Aufarbeitung

  1. stirringstirred for 13 minutes
  2. stirringstirred at room temperature for 30 minutes
  3. washAfter the reaction mixture was washed with water and aqueous saturated sodium bicarbonate solution
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=10:1)
  7. customto yield a crude product
  8. customThe crude product was recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-d4cf7afa31954f7aaa77507c51625fd1
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313153B1

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