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Piperidine → Methyl 3-(1-(2-acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2propenoate

HRID 1089432
ノート
印刷プレビュー

反応式

HRID 1089432 の反応式
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([O-])=O.[C:9]([NH:12][CH2:13][CH2:14][N:15]1[C:19]([CH3:20])=[CH:18][C:17](C=O)=[C:16]1[CH3:23])(=[O:11])[CH3:10].N1CCCCC1>N1C=CC=CC=1>[C:9]([NH:12][CH2:13][CH2:14][N:15]1[C:16]([CH3:23])=[CH:17][C:18]([CH:3]=[CH:2][C:1]([O:7][CH3:8])=[O:6])=[C:19]1[CH3:20])(=[O:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8082PiperidineHCID 178134N-(2-(3-Formyl-2,5-dimethyl-1H-pyrrol-1-yl)ethyl)acetamideHCID 3801157Monomethyl malonate2 回

生成物 1

HCID 53938375Methyl 3-(1-(2-acetylaminoethyl)-2,5-dimethylpyrrol-3-yl)-2propenoate収率 56.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

6.1 g (0.05 mol) of monomethyl malonate are dissolved in 20 ml of pyridine. After addition of 10.4 g (0.05 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole-3-aldehyde (see Example 13) and 1 ml of piperidine, the mixture is heated under reflux for 15 hours. After addition of a further 27 g of monomethyl malonate, heating is continued for a further 24 hours, the mixture is concentrated, the residue is taken up in water, the mixture is extracted with methylene chloride and the methylene chloride phase is washed with dilute acid and alkali and concentrated. Column chromatography with methylene chloride:methanol=98:2 as the mobile phase gives 7.5 g of product, which can be recrystallized from ethyl acetate.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 15 hours
  3. temperatureheating
  4. concentrationthe mixture is concentrated
  5. extractionthe mixture is extracted with methylene chloride
  6. washthe methylene chloride phase is washed
  7. additionwith dilute acid
  8. concentrationalkali and concentrated

出典と根拠

ORDレコード
ord-02c9651e9d414fd2b76b877bd5afd129
出典データセット
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04966901

反応ノート

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