1,1'-Carbonyldiimidazole → 1-(1H-imidazol-1-ylcarbonyl)-4-(3-phenylpropanoyl)piperazine

HRID 384457Notes

Reaction equation

HRID 384457 reaction equation
Cl.[C:2]1([CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]>C(#N)C>[N:20]1([C:18]([N:15]2[CH2:14][CH2:13][N:12]([C:10](=[O:11])[CH2:9][CH2:8][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:17][CH2:16]2)=[O:19])[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 685064511-(3-Phenylpropanoyl)piperazine hydrochloride

Product 1

HCID 595270961-(1H-imidazol-1-ylcarbonyl)-4-(3-phenylpropanoyl)piperazineYield 92.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Phenylpropanoyl)piperazine hydrochloride (1.0 g) was dissolved in acetonitrile, and 1,1′-carbonyldiimidazole (950 mg) was added thereto at room temperature, followed by stirring at the same temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5) to obtain 1-(1H-imidazol-1-ylcarbonyl)-4-(3-phenylpropanoyl)piperazine (1.13 g).

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-1b567b6b820f4a91ad6b3cf598c6e574
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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