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

HRID 377910Notes

Reaction equation

HRID 377910 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+].Br[CH2:31][CH:32]1[CH2:34][CH2:33]1>CN(C)C=O>[CH:32]1([CH2:31][N:11]([C:4]2[C:5]([O:9][CH3:10])=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[C:12]([N:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:18][CH2:19]2)=[O:13])[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 193571181-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine

Product 1

HCID 193569611-[N-Cyclopropylmethyl-N-(5,6-dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(2-methoxyphenyl)piperazine(100 mg, 0.26 mmol) was dissolved in dimethylformamide(15 ml) and thereto sodium hydride(6.2 mg, 0.26 mmol) was added, followed by stirring at room temperature for 15 min, and successively bromomethylcyclopropane(21.8 mg, 0.26 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-ce8d7809756446409236b54a2ab8ba83
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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