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

HRID 36854

반응식

HRID 36854 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-f317d4907b7246d2bd8a17afb1447994
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418229

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