Hydrochloric Acid → (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

HRID 976125ノート

反応式

HRID 976125 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[CH:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]([C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 570097054-[3-(1-Benzylpiperidin-4-yl)propenoyl]nitrobenzene

生成物 1

HCID 19968908(E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

1.27 g of 4-[3-(1-benzylpiperidin-4-yl)propenoyl]-nitrobenzene was added to a mixed solution of 10 ml of acetic acid and 2 ml of hydrochloric acid, and then 1.38 g of stannous chloride was added thereto under ice cooling. The mixture was stirred for 24 hours while further adding 0.69 g of stannous chloride twice during the reaction. The solvent was removed under reduced pressure to obtain a crude product of (E)-4-[3-(1-benzylpiperidin-4-yl)propenoyl]aniline. Then, this was dissolved in 15 ml of ethanol, and to the solution was added 0.67 g of 4-chloro-5,6-dimethylpyrimidine. Subsequently, the mixture was reacted by heating at 60° C. for 30 minutes. The reaction mixture was neutralized by adding a 28% sodium methylate-methanol solution under cooling, solids were removed by filtration, and then the filtrate was consensed under reduced pressure. The obtained residue was applied to silica gel column chromatography to obtain 1.02 g of the title compound as pale yellow powder.

後処理

  1. customtwice during the reaction
  2. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-cbccf30b9419449380fa94a0ea80d186
出典データセット
uspto-grants-1997_03
特許番号
US05610303

反応ノート

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