1-Ethylcyclopentene → 7-(2-Ethyl-1-piperidinyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235560
[CH2:1]([C:3]1[CH2:7][CH2:6][CH2:5][CH:4]=1)[CH3:2].C(=O)(O)[O-].[Na+].[NH2:13][C:14]1[C:19]2[N:20]([CH3:24])[C:21](=[O:23])[NH:22][C:18]=2[CH:17]=[CH:16][CH:15]=1.[H][H]>CO.[Pd]>[CH2:1]([CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4][N:13]1[C:14]1[C:19]2[N:20]([CH3:24])[C:21](=[O:23])[NH:22][C:18]=2[CH:17]=[CH:16][CH:15]=1)[CH3:2]

Komponenten

7

Edukt 4

HCID 1374481-EthylcyclopenteneHCID 516892Sodium BicarbonateHCID 596354197-Amino-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 685810967-(2-Ethyl-1-piperidinyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-ethylcyclopentene (1.0 g, 10.4 mmol) and sodium bicarbonate (0.1 g, 1.19 mmol) in methanol (150 ml) was ozonized at −78° C. until TLC analysis indicated complete consumption of 1-ethylcyclopentene. The crude ozonide was transferred directly to a mixture of 7-amino-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (0.5 g, 3.07 mmol) and 10% palladium on carbon (0.05 g, Degussa type; 50% wet). The flask was fitted with a balloon of hydrogen and allowed to stir for 12 h. The reaction was filtered through GF/F paper and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography eluting with a 10% acetone/hexanes mixture to afford 597 mg (75%) of the title compound.

Aufarbeitung

  1. customwas ozonized at −78° C. until TLC analysis
  2. customconsumption of 1-ethylcyclopentene
  3. filtrationThe reaction was filtered through GF/F paper
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with a 10% acetone/hexanes mixture

Quellen und Nachweise

ORD-Eintrag
ord-067988451bd74655a05dd717b5b777b4
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07714009B2

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