Sodium Chloride → 4-Nitro-N-[2-(4-benzoyl-1-piperidinyl)ethyl]-N-(3-pyridyl)benzamide

HRID 2517

反応式

HRID 2517 の反応式
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1.[I-].[Na+].[Cl-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([N:10]([CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([C:30](=[O:37])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:28][CH2:29]2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

7

反応物 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 83332Pyridine, 3-(p-nitrobenzamido)-HCID 10824664(1-(2-Chloroethyl)piperidin-4-yl)(phenyl)methanone

生成物 1

HCID 196900494-Nitro-N-[2-(4-benzoyl-1-piperidinyl)ethyl]-N-(3-pyridyl)benzamide収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

In an atmosphere of argon, 4-nitro-N-(3-pyridyl)benzamide (973 mg, 4.00 mmol) was dissolved in DMF (10 ml) to which was subsequently added sodium hydride (176 mg, 60%, 4.40 mmol) at room temperature, stirred for 1 hour at 60° C., and added dropwise 1-(2-chloroethyl)-4-benzoylpiperidine (1.38 g, 5.49 mmol) and a catalytically effective amount of a DMF solution (12 ml) of sodium iodide. After 4 hours of stirring at 60° C., the reaction solution was mixed with saturated sodium chloride aqueous solution and extracted with ethyl acetate. The resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order, and dried on anhydrous sodium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was purified by recrystallization (ethyl acetate-ether) to obtain 439.6 mg (24.0%) of the title compound in a light yellow powder form.

後処理

  1. customat room temperature
  2. stirringAfter 4 hours of stirring at 60° C.
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with saturated sodium chloride aqueous solution and water in that order
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThereafter, the solvent was removed by evaporation
  7. customthe resulting residue was purified by recrystallization (ethyl acetate-ether)

出典と根拠

ORDレコード
ord-210fb1b1e78248f89d667958215bdb36
出典データセット
uspto-grants-1998_03
特許番号
US05728835

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