Sodium Carbonate → HCID 15087792, Verbindung

HRID 1073165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073165
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[C:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)=[O:8].[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][N:24]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:6]([C:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][N:27]2[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:23]([CH3:22])[CH2:28]2)=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 15087784tert-Butyl 2-methylpiperazine-1-carboxylateHCID 15087790N-(4-Chlorobutyl)-N-(4-fluorophenyl)-3-pyridinecarboxamide

Produkt 1

HCID 15087792HCID 15087792, VerbindungAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5 parts of N-(4-chlorobutyl)-N-(4-fluorophenyl)-3-pyridinecarboxamide, 2.77 parts of (1,1-dimethylethyl) 2-methyl-1-piperazinecarboxylate, 1.58 parts of sodium carbonate and 94 parts of N,N-dimethylformamide was stirred for 48 hours at 90° C. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted twice with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) as eluent. The first fraction was collected and the eluent was evaporated, yielding 3.5 parts (57.2%) of (1,1-dimethylethyl) 4-[4-[(4-fluorophenyl)(3-pyridinylcarbonyl)amino]butyl]-2-methyl-1-piperazinecarboxylate as a residue (int. 43).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. extractionThe product was extracted twice with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (96:4 by volume) as eluent
  9. customThe first fraction was collected
  10. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6c4ee06b84424d6e9a31040b37824cea
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968684

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