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

HRID 728914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728914
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

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) andmethylene 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.

Aufarbeitung

  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) andmethylene 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

Quellen und Nachweise

ORD-Eintrag
ord-9226d408ad814af2a864dcc269811253
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051422

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