1,1'-Carbonyldiimidazole → HCID 86747983, compound

HRID 1729020Notes

Reaction equation

HRID 1729020 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.[C:13]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)(N1C=CN=C1)=O.[C:25]([C:28]1[CH:33]=[CH:32][C:31](N2CCNCC2)=[CH:30][CH:29]=1)(=[O:27])[CH3:26]>CN(C)C=O>[C:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:20]1[CH2:13][CH2:21][N:22]([C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)=[O:12])[CH2:23][CH2:24]1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 742811H-Indole-7-carboxylic acidHCID 97269Piperazin-4-ylacetophenone

Product 1

HCID 86747983HCID 86747983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of indole-7-carboxylic acid (3.22 g; 20 mmoles) in 30 ml dimethylformamide was added 1,1'-carbonyldiimidazole (3.24 g; 20 mmoles). This was stirred for 50 minutes at ice bath temperature at which time 4-(4-acetylphenyl)piperazine was added to the reaction. This was stirred for 2 hours at ambient temperature. The solvent was then concentrated off and the resulting oil was triturated with water and filtered to give a solid. The solid was recrystallized from methanol:waterto give 5.31 g (76%) of 4-(4-(Acetylphenyl)-1-(1H-indol-7-ylcarbonyl)piperazine, m.p. 189°-191° C.

Workup

  1. additionwas added to the reaction
  2. concentrationThe solvent was then concentrated off
  3. customthe resulting oil was triturated with water
  4. filtrationfiltered
  5. customto give a solid
  6. customThe solid was recrystallized from methanol

Sources & evidence

ORD record
ord-f823ef3129544538a7f7e331a9833bdc
Source dataset
uspto-grants-1994_07
Patent number
US05330986

Reaction notes

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