Acetic Acid → (+/-)-(5-Amino-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide

HRID 1987760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987760
[N+:1]([C:4]1[CH:33]([CH3:34])[CH:8]2[CH2:9][C:10]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH:32]=[CH:31][N:30]=[CH:29]5)=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])([CH3:12])[O:11][C:7]2=[C:6]([CH3:35])[C:5]=1[CH3:36])([O-])=O.C(O)C.C(O)(=O)C.[OH-].[Na+]>[C].[Pd].O>[NH2:1][C:4]1[CH:33]([CH3:34])[CH:8]2[CH2:9][C:10]([NH:13][C:14]([N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH:32]=[CH:31][N:30]=[CH:29]5)=[CH:24][CH:23]=4)[CH2:20][CH2:21]3)=[O:15])([CH3:12])[O:11][C:7]2=[C:6]([CH3:35])[C:5]=1[CH3:36]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 68849562(+/-)-(5-Nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide

Produkt 1

HCID 68848816(+/-)-(5-Amino-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamideAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

In an autoclave, 0.88 g of (±)-(5-nitro-2,4,6,7-tetramethyldihydrobenzofuran-2-yl)-[4-(4-imidazol-1-ylphenyl)-piperazin-1-yl]carboxamide and 0.5 g of 10% palladium carbon, 10 ml of ethanol and 5 ml of acetic acid were added, followed by stirring overnight under a hydrogen pressure of 10 kg/cm2. The reaction solution was poured into water, neutralized with a 1N sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:methanol=10:1) to obtain 0.56 g of the objective product (melting point: 189-191° C.).

Aufarbeitung

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationconcentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1718f495fa0847cea0b200c08883da3b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553837B2

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