Sodium hydride → 1-[N-Cyclopropylmethyl-N-(2-methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377885Notes

Reaction equation

HRID 377885 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+].Br[CH2:35][CH:36]1[CH2:38][CH2:37]1>CN(C)C=O>[CH:36]1([CH2:35][N:13]([C:12]2[C:3]([O:2][CH3:1])=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)[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])[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 193569681-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

Product 1

HCID 193570941-[N-Cyclopropylmethyl-N-(2-methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(2-methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(106 mg, 0.25 mmol) was dissolved in dimethylformamide(15 ml) and sodium hydride(6.2 mg, 0.26 mmol) was added and the solution was stirred at room temperature for 15 min. Bromomethylcyclopropane(22 mg, 0.26 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-a5536ac89ba04ea0b580e08bddf216b0
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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