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Benzyl Bromide → 1-[N-Benzyl-N-(2-methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377886
Notes
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Reaction equation

HRID 377886 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+].[CH2:34](Br)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C)C=O>[CH2:34]([N:13]([C:12]1[C:3]([O:2][CH3:1])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([O:30][CH3:31])[CH:23]=2)[CH2:18][CH2:17]1)=[O:15])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 193569681-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

Product 1

HCID 193572031-[N-Benzyl-N-(2-methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 90%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

1-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(114 mg, 0.27 mmol) was dissolved in dimethylformamide(15 ml) and sodium hydride(6.6 mg, 0.27 mmol) was added and the solution was stirred at room temperature for 15 min. Benzylbromide(46 mg, 0.27 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. stirringThe mixture was stirred at room temperature for 16 hours
  2. concentrationconcentrated under the reduced pressure
  3. customto remove dimethylformamide
  4. customThe concentrate was purified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-e37e9d8f78814add9be3437e860f5f7f
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06028195

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes