1-Phenylpiperazine → HCID 19013292, compound

HRID 1729019Notes

Reaction equation

HRID 1729019 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]1([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([N:22]2[CH2:23][CH2:24][N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20][CH2:21]2)=[O:12])[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 742811H-Indole-7-carboxylic acid

Product 1

HCID 19013292HCID 19013292, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Indole-7-carboxylic acid (3.20 g, 0.02 mole) was dissolved in 30 ml of dimethylformamide (DMF) and chilled with ice-water. N,N'-Carbonyldiimidazole (3.30 g, 0.02 mole) was then added and the reaction mixture was allowed to stir for 1 hour. At the end of this time N-phenylpiperazine (4.0 g, 0.025 mole) was added, the cold bath was removed., and the reaction mixture was allowed to come to room temperatureover 3 hours. The product was filtered off and recrystallized form toluene to give 3.30 g (54%) of 1-(1H-indol-7-ylcarbonyl)-4-phenylpiperazine, m.p.217°-219° C.

Workup

  1. customthe cold bath was removed
  2. waitto come to room temperatureover 3 hours
  3. filtrationThe product was filtered off
  4. customrecrystallized
  5. customform toluene

Sources & evidence

ORD record
ord-d232fcf06538482ebcb02ff930d7944a
Source dataset
uspto-grants-1994_07
Patent number
US05330986

Reaction notes

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