Acetic Acid → HCID 58998518, Verbindung

HRID 1592998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592998
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[CH3:26][S:23]([C:21]1[CH:20]=[CH:19][C:18]2[N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:15]=[N:16][C:17]=2[CH:22]=1)(=[O:25])=[O:24]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 687092041-(1-benzylpiperidin-4-yl)-5-methylsulphonyl-1H-benzimidazole

Produkt 1

HCID 58998518HCID 58998518, VerbindungAusbeute 793,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The crude material from step 3 (10 g) was dissolved in 1 litre of methanol in a pressure vessel, 20 g of moist 10% Pd/C catalyst and 100 mL acetic acid were added and stirred under an atmosphere of hydrogen at 5 bar and 50° C. for 8 hours. The reaction was cooled, filtered and evaporated. The residue was dissolved in water and basified with sodium hydroxide solution, extracted into dichloromethane, dried and evaporated. The brown solid was triturated with isopropanol, filtered, and washed with ether to give the title compound (60 g) as a pale grey solid; NMR: 2.00(m, 4H), 2.75(m, 2H), 3.15(m, 2H), 3.20(s, 3H), 4.60(m, 1H), 7.78 (dd, 1H), 7.85(d, 1H), 8.20(d, 1H), 8.56(s, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. customevaporated
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted into dichloromethane
  6. customdried
  7. customevaporated
  8. customThe brown solid was triturated with isopropanol
  9. filtrationfiltered
  10. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-80071eab113847ed91e78c28a618e3aa
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294636B2

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