1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → ethyl 2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethylcarbamate

HRID 437622

Reaktionsgleichung

Reaktionsgleichung von HRID 437622
Br[CH2:2][CH2:3][NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8].[NH:10]1[CH2:15][CH2:14][CH:13]([N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]2=[O:25])[CH2:12][CH2:11]1.C(=O)([O-])O.[Na+]>C(O)C>[O:25]=[C:17]1[N:16]([CH:13]2[CH2:12][CH2:11][N:10]([CH2:2][CH2:3][NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH2:15][CH2:14]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18]1

Komponenten

5

Edukt 3

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 286694ethyl N-(2-bromoethyl)carbamateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 21428897ethyl 2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 12.94 parts of ethyl (2-bromoethyl)carbamate, 13.51 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.1 parts of sodium hydrogen carbonate and 160 parts of ethanol is stirred and refluxed overnight. The reaction mixture is cooled, filtered over hyflo and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane, 10% of methanol and one drop of ammonium hydroxide, as eluent. The pure fractions are collected and the eluent is evaporated, yielding 4.4 parts of ethyl 2-[4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]ethylcarbamate as a residue.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered over hyflo
  4. customthe filtrate is evaporated
  5. customThe residue is purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane, 10% of methanol and one drop of ammonium hydroxide
  7. customThe pure fractions are collected
  8. customthe eluent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-73c8c05ebae646fc8d699fc2200a374d
Quelldatensatz
uspto-grants-1977_06
Patentnummer
US04031226

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