Water → (R)-3-acetyl-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-one

HRID 230464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 230464
[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Na+].[C:31](Cl)(=[O:33])[CH3:32].O>CN(C=O)C>[C:31]([N:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N:19]([CH:16]2[CH2:17][CH2:18][N:13]([C@H:1]3[C:11]4=[C:12]5[C:7](=[CH:8][CH:9]=[CH:10]4)[CH:6]=[CH:5][CH:4]=[C:3]5[CH2:2]3)[CH2:14][CH2:15]2)[C:20]1=[O:28])(=[O:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 10287064(R)-1-(1-(1,2-Dihydroacenaphthylen-1-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one

Produkt 1

HCID 67331504(R)-3-acetyl-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-oneAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(R)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-benzoimidazol-2-one (6.2 g, 16.8 mmol) was dissolved in DMF (60 ml). Sodium hydride (0.9 g, 60%) was added and the suspension was stirred at 50° C. for 30 min. It was cooled to room temperature and acetyl chloride (1.5 g, 19 mmol) was added and the mixture was stirred for 3 hr. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated aqueous ammonium chloride solution, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (6.3 g) as pale-yellow crystals

Aufarbeitung

  1. temperatureIt was cooled to room temperature
  2. stirringthe mixture was stirred for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water and saturated aqueous ammonium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-9fb6721f66cf43f6b7962aa60e0f84f4
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566728B2

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