Methyl iodide → 1-[N-(2-Methoxyquinolin-3-yl)-N-methylaminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377883Notes

Reaction equation

HRID 377883 reaction equation
[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[H-].[Na+].I[CH3:35]>>[CH3:1][O:2][C:3]1[C:12]([N:13]([CH3:35])[C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 193569681-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

Product 1

HCID 193570001-[N-(2-Methoxyquinolin-3-yl)-N-methylaminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 93%

Procedure

1-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(106 mg, 0.25 mmol) was dissolved in dimethylfonnamide(15 ml) and sodium hydride(6.0 mg, 0.25 mmol) was added and the solution was stirred at room temperature for 15 min. Iodomethane(35 mg, 0.25 mmol) was added to the above solution. The mixture was stirred at room temperature for 16 hours and concentrated under the reduced pressure to remove dimethylformamide. The concentrate was purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 16 hours
  3. concentrationconcentrated under the reduced pressure
  4. customto remove dimethylformamide
  5. customThe concentrate was purified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-4a43a2150b174a72b6b234ad90b5b404
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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