5-Methoxyindoleacetic acid → 1-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazine

HRID 1250073Notes

Reaction equation

HRID 1250073 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([OH:27])=O.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1)([O-:30])=[O:29]>C1COCC1.CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([N:40]1[CH2:41][CH2:42][N:37]([C:34]2[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=2)[CH2:38][CH2:39]1)=[O:27]

Participants

6

Reactant 3

HCID 189865-Methoxyindoleacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 219187071-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazineYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml flask, 1.62 g (10 mmoles) of 1.1′-carbonyl-diimidazole is added to a solution of 2.05 g (10 mmoles) of 5-methoxyindole-3-acetic acid in 10 ml of THF. After one hour of agitation at ambient temperature, a solution of 1-(4-nitrophenyl)piperazine in 10 ml of DMF is added dropwise. Agitation is continued for 15 hours. The reaction medium is then concentrated under vacuum and the evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1). After filtration, the solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane. After drying under vacuum, a yellow powder is obtained with a yield of 91%. Melting point: 239-240° C.

Workup

  1. waitAgitation is continued for 15 hours
  2. concentrationThe reaction medium is then concentrated under vacuum
  3. customthe evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1)
  4. filtrationAfter filtration
  5. washthe solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane
  6. customAfter drying under vacuum
  7. customa yellow powder is obtained with a yield of 91%

Sources & evidence

ORD record
ord-8a8dbd518b0a4e7eb84df2c6f0a12c0e
Source dataset
uspto-grants-2002_01
Patent number
US06335445B1

Reaction notes

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