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Formaldehyde → 1-[[1,5-Bis(4-chlorophenyl)-2-methyl-pyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine

HRID 638798
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 638798
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Cl.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[C:26]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1.[CH2:38]=O.[OH-].[Na+]>C(#N)C.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:10][C:11]([CH2:38][N:33]3[CH2:34][CH2:35][N:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:36])[F:37])[CH:25]=4)[CH2:31][CH2:32]3)=[C:12]2[CH3:13])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 4569171,2-Bis(4-chlorophenyl)-5-methylpyrroleHCID 3084246TFMPP hydrochloride

Produkt 1

HCID 30113901-[[1,5-Bis(4-chlorophenyl)-2-methyl-pyrrol-3-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazineAusbeute 66,24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of 1,2-bis(4-chlorophenyl)-5-methylpyrrole (1.76 g, 0.006 mol, as obtained in Step-2) in acetonitrile (18 ml) was added a mixture of 1-(3-trifluoromethylphenyl)piperazine hydrochloride (1.55 g, 0.006 mol), 40% formaldehyde (0.45 ml, 0.006 mol) and acetic acid (5.23 ml) drop-wise. After the completion of addition, the reaction mixture was stirred at room temperature for 3-4 hours. The reaction mixture was neutralized with NaOH (20% aq. soln.) and extracted with ethyl acetate (2×100 ml). The combined ethyl acetate extract was washed with water (2×50 ml), brine (1×30 ml), dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was purified by column chromatography over silica gel using ethyl acetate hexane (80:10) as eluent to give 2.1 g (66.24%) of the title compound.

Aufarbeitung

  1. additionAfter the completion of addition
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water (2×50 ml), brine (1×30 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent evaporated off
  7. customThe crude product so obtained
  8. customwas purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-757b52a9903b47b1ac59e4054dfe87ab
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691837B2

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