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

HRID 1681744Notes

Reaction equation

HRID 1681744 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-1d692a838e9e40a4b27a9d7a3172cef8
Source dataset
uspto-grants-1992_12
Patent number
US05173493

Reaction notes

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