Benzyl Chloride → 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one

HRID 486222노트

반응식

HRID 486222 반응식
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][CH:8]1[C:20](=[O:21])[N:12]2[C:13]3[C:18]([CH:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[CH:15][CH:14]=3.[H-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.O>[CH2:24]([N:6]1[C:2]([CH3:1])=[C:3]([CH2:7][CH:8]2[C:20](=[O:21])[N:12]3[C:13]4[C:18]([CH:19]=[C:11]3[CH2:10][CH2:9]2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:4]=[CH:5]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 102656158,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one

생성물 1

HCID 190973117-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one수율 70.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of 8,9-dihydro-7-[(5-methyl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (500 mg) in N,N-dimethylformamide (5 ml) at room temperature was added sodium hydride (60% in mineral oil, 79 mg). After stirring at room temperature for 10 minutes and then at 5° C. for 5 minutes, the solution was treated with a solution of benzyl chloride (249 mg) in N,N-dimethylformamide (1 ml) at 5° C. The mixture was stirred at 5° C. for 10 minutes and then at room temperature for 2 hours. The reaction mixture was diluted with chilled water and extracted twice with chloroform. The chloroform layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The oil obtained was purified by silica gel column chromatography (1% methanol-chloroform) to give 7-[(1-benzyl-5-methyl-1H-imidazol-4-yl)methyl]-8,9-dihydropyrido[1,2-a]indol-6(7H)-one (468 mg).

후처리

  1. waitat 5° C. for 5 minutes
  2. stirringThe mixture was stirred at 5° C. for 10 minutes
  3. waitat room temperature for 2 hours
  4. extractionextracted twice with chloroform
  5. washThe chloroform layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe oil obtained
  9. customwas purified by silica gel column chromatography (1% methanol-chloroform)

출처 및 근거

ORD 기록
ord-ecc39c6e3dd147cfa9221a52d6e55012
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290785

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