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

HRID 987023

Reaktionsgleichung

Reaktionsgleichung von HRID 987023
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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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%

Quellen und Nachweise

ORD-Eintrag
ord-ac404678a13541dc8ad5ff7a0c2b08eb
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630461B2

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