Benzyl Bromide → 1-[N-Benzyl-N-(5,6-dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine

HRID 377909Notes

Reaction equation

HRID 377909 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH2:30]([N:11]([C:4]1[C:5]([O:9][CH3:10])=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1)[C:12]([N:14]1[CH2:15][CH2:16][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH2:18][CH2:19]1)=[O:13])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 193571181-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine

Product 1

HCID 193570351-[N-Benzyl-N-(5,6-dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazineYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine(100 mg, 0.27 mmol) was dissolved in dimethylformamide(15 ml) and thereto sodium hydride(6.5 mg, 0.27 mmol) was added, followed by stirring at room temperature for 1 hr, and successively benzyl bromide(46.2 mg, 0.27 mmol) was added. The resulting mixture was stirred at room temperature for 16 hrs, concentrated under the reduced pressure and purified by column chromatography(ethylacetate:hexane=1:2) to obtain the titled compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 hrs
  2. concentrationconcentrated under the reduced pressure
  3. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-f7e3688db4de44eaad287048ac41f6e4
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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