Dimethylformamide → 4-(1H-Imidazol-1-yl)-N-[[4-phenyl-1-(phenylmethyl)piperazin-2-yl]methyl]benzamide

HRID 1588970ノート

反応式

HRID 1588970 の反応式
CN(C)C=O.[N:6]1([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)[CH:10]=[CH:9][N:8]=[CH:7]1.[C:20]1([N:26]2[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:28]([CH2:39][NH2:40])[CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(Cl)Cl>C(N(CC)CC)C.CO>[N:6]1([C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:40][CH2:39][CH:28]3[CH2:27][N:26]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:31][CH2:30][N:29]3[CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:17])=[CH:18][CH:19]=2)[CH:10]=[CH:9][N:8]=[CH:7]1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 7365294-(1-Imidazolyl)benzoic AcidHCID 11044210C-(1-Benzyl-4-phenyl-piperazin-2-yl)-methylamine

生成物 1

HCID 149987954-(1H-Imidazol-1-yl)-N-[[4-phenyl-1-(phenylmethyl)piperazin-2-yl]methyl]benzamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

To N,N-dimethylformamide (200 mL) under nitrogen atmosphere add 4-(1H-imidazol-1-yl)benzoic acid (7.0 g, 37 mmol) and 1,1-carbonyldiimidazole (6.0 g, 37 mmol) and stir for 1 h. Add 4-phenyl-1-(phenylmethyl)-2-piperazinemethanamine (9.5 g, 34 mmol) and stir. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction remove the solvent in vacuo. To the oil add water (100 mL), a saturated solution of sodium bicarbonate (30 mL) and methylene chloride (200 mL) and stir for 1 h. Separate the layers and extract the aqueous layer with methylene chloride. Concentrate the combined organic layers to give an oil. Flash chromatograph the oil on silica (1000 g) with a mixture of methylene chloride, methanol, triethylamine (97/2/1). Combine and concentrate the fractions containing product. Recrystallize the solid from ethyl acetate/hexane to provide the title compound.

後処理

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customUpon completion of the reaction remove the solvent in vacuo
  3. additionTo the oil add water (100 mL)
  4. stirringa saturated solution of sodium bicarbonate (30 mL) and methylene chloride (200 mL) and stir for 1 h
  5. customSeparate the layers
  6. extractionextract the aqueous layer with methylene chloride
  7. concentrationConcentrate the combined organic layers
  8. customto give an oil
  9. concentrationCombine and concentrate the fractions
  10. additioncontaining product
  11. customRecrystallize the solid from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-71a99ab021a44405b7b64a9fb123f402
出典データセット
uspto-grants-1993_06
特許番号
US05223623

反応ノート

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