Sodium hydride → 1-[(2-Methoxyquinoxalin-3-yl)N-isopropylaminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 1841485Notes

Reaction equation

HRID 1841485 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])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[H-].[Na+].[CH2:34](I)[CH2:35][CH3:36]>CN(C)C=O>[CH3:1][O:2][C:3]1[C:12]([N:13]([CH:35]([CH3:36])[CH3:34])[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])=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 98669701-[(2-Methoxyquinoxalin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

Product 1

HCID 234463001-[(2-Methoxyquinoxalin-3-yl)N-isopropylaminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1-[(2-methoxyquinoxalin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine (216 mg, 0.51 mmol) dissolved in dimethylformamide (20 ml), 60% sodium hydride (20.4 mg, 0.51 mmol) was added and stirred at room temperature for 15 minutes, and thereto propyl iodide (86.7 mg, 0.51 mmol) was added. The resulting mixture was stirred at room temperature for 6 hours, concentrated under the reduced pressure to remove the solvent and purified by column chromatography to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 6 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove the solvent
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-beb80fc91dc9436fa2a92293577a49e1
Source dataset
uspto-grants-2004_01
Patent number
US06683184B2

Reaction notes

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