Isopropyl iodide → HCID 19357154, compound

HRID 377908Notes

Reaction equation

HRID 377908 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]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([O:28][CH3:29])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].I[CH:33]([CH3:35])[CH3:34]>CN(C)C=O>[CH:33]([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[CH2:19][CH2:18][N:17]([C:20]2[CH:21]=[C:22]([O:28][CH3:29])[CH:23]=[C:24]([O:26][CH3:27])[CH:25]=2)[CH2:16][CH2:15]1)=[O:13])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 17893214HCID 17893214, compound

Product 1

HCID 19357154HCID 19357154, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-[(5,6-Dimethyl-2-methoxypyridin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine(100 mg, 0.25 mmol) was dissolved in dimethylformamide(15 ml) and thereto sodium hydride(6.0 mg, 0.25 mmol) was added, followed by stirring at room temperature for 15 min, and then 2-iodopropane(42 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 16 hrs, concentrated under the reduced pressure to remove dimethylformamide, 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. customto remove dimethylformamide
  4. custompurified by column chromatography(ethylacetate:hexane=1:2)

Sources & evidence

ORD record
ord-972021b76ae9440e97ec447ec29a3d4f
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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