Water → HCID 21716323, compound

HRID 1385907Notes

Reaction equation

HRID 1385907 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[O:16][CH2:15][C:14](=[O:17])[NH:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:20]I.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[O:16][CH2:15][C:14](=[O:17])[N:13]([CH3:20])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15545704HCID 15545704, compound

Product 1

HCID 21716323HCID 21716323, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3,4-dimethoxyphenyl)morpholin-5-one (0.10 g, 0.42 mM) produced in Example 1, sodium hydride (60%) (0.02 g, 0.46 mM), and methyl iodide (0.07 g, 0.51 mM) were dissolved in dry N,N-dimethylformamide (2 ml) and the mixture was stirred at room temperature for one night. Water was added to the reaction solution, the solution was extracted with methylene chloride, the extract was dried over anhydrous sodium sulfate, then the solvent was removed in vacuo to obtain a crude product as a yellow oil. The crude product was purified by flash chromatography (SiO2: eluted by 3% methanol/methylene chloride) to obtain the above-described compound (yield 96.9%) as a colorless solid.

Workup

  1. extractionthe solution was extracted with methylene chloride
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customto obtain a crude product as a yellow oil
  5. customThe crude product was purified by flash chromatography (SiO2: eluted by 3% methanol/methylene chloride)

Sources & evidence

ORD record
ord-3cecc7a7eaac47c59b266c67ceb59901
Source dataset
uspto-grants-2001_07
Patent number
US06265402B1

Reaction notes

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