Ammonium → 1-Acetyl-4-(4-imidazol-1-ylphenyl)-piperazine

HRID 1987755Notes

Reaction equation

HRID 1987755 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C1(C=CC(=O)C=CC2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+]>C1(C)C(C)=CC=CC=1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 223AmmoniumHCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 138219171-(4-(4-Bromophenyl)piperazin-1-YL)ethanone

Product 1

HCID 231182961-Acetyl-4-(4-imidazol-1-ylphenyl)-piperazineYield 79.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
125 °C

Procedure

To a reaction solution prepared by dissolving 20 g of 1-acetyl-4-(4-bromophenyl)-piperazine and 7.9 g of imidazole in 120 ml of xylene, 16.9 g of 1,10-phenanthroline, 1.4 g of 1,5-diphenyl-1,4-pentadien-3-one, 28.9 g of cesium carbonate and 1.8 g of a copper (I) trifluoromethanesulfonate benzene complex, as a catalyst, were added at room temperature, followed by heating at reflux in an argon gas flow at 125° C. for 24 hours. After the completion of the reaction, the reaction solution was mixed with 300 ml of an aqueous ammonium solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:ethyl acetate=3:1→chloroform:methanol=20:1) to obtain 15.2 g of the objective 1-acetyl-4-(4-imidazol-1-ylphenyl)-piperazine (melting point: 181-182° C.).

Workup

  1. customTo a reaction solution prepared
  2. additionas a catalyst, were added at room temperature
  3. temperatureby heating
  4. customAfter the completion of the reaction
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing magnesium sulfate
  9. filtrationby filtration
  10. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-369b446eca72455a8f872d990ce72911
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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