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

HRID 428139

反応式

HRID 428139 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 20701373(E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamide収率 56.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d4cf7afa31954f7aaa77507c51625fd1
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

関連ノート

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