Sodium Bicarbonate → 5-{3-[N-(4-Methylphenethyl)-N-methylamino]propionyl}-10,11-dihydrodibenzo [b,e][1,4]diazepin-11-one

HRID 36854

Reaktionsgleichung

Reaktionsgleichung von HRID 36854
[CH3:1][NH:2][CH2:3][CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[CH:22][C:8]1=2)=[O:6].[CH3:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29][N:2]([CH2:3][CH2:4][C:5]([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][C:9]3[CH:19]=[CH:20][CH:21]=[CH:22][C:8]2=3)=[O:6])[CH3:1])=[CH:26][CH:25]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 5706804-Methylphenethyl bromideHCID 208028975,10-Dihydro-5-[3-(methylamino)-1-oxopropyl]-11H-dibenzo[b,e][1,4]diazepin-11-one

Produkt 1

HCID 539939905-{3-[N-(4-Methylphenethyl)-N-methylamino]propionyl}-10,11-dihydrodibenzo [b,e][1,4]diazepin-11-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5-(3-methylaminopropionyl)-10,11-dihydrodibenzo [b,e][1,4]diazepin-11-one (0.20 g) (J. Med. Chem., 1963, 6, 255), 4-methylphenethyl bromide (0.14 g) and sodium hydrogen carbonate (60 mg) in acetonitrile (20 ml) was heated under reflux for 16 hours and evaporated. The residue was partitioned between water and dichloromethane and the organic layer washed with brine, dried over MgSO4 and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 0-20% methanol as eluant. Appropriate fractions were combined and evaporated and the residue crystallised from ether to give the title compound as a colourless solid, 60 mg (21%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated
  4. customThe residue was partitioned between water and dichloromethane
  5. washthe organic layer washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica
  9. customevaporated
  10. customthe residue crystallised from ether

Quellen und Nachweise

ORD-Eintrag
ord-f317d4907b7246d2bd8a17afb1447994
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418229

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