Methylamine → Methyl N-(3-methoxy-3-oxopropyl)-N-methyl-beta-alaninate

HRID 41809Notes

Reaction equation

HRID 41809 reaction equation
C(=O)=[O:2].CC(C)=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14]C(O)=CC=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].[CH3:23][NH2:24]>>[CH3:23][N:24]([CH2:14][CH2:15][C:10]([O:9][CH3:8])=[O:2])[CH2:19][CH2:18][C:17]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 7294Methyl Acrylate2×HCID 90154-MethoxyphenolHCID 18522661Acetone cardice

Product 1

HCID 66925Methyl N-(3-methoxy-3-oxopropyl)-N-methyl-beta-alaninate

Procedure

Into a 3 L round bottom flask cooled in a water bath and equipped with an overhead stirrer, thermometer, gas inlet tube and a solid carbon dioxide/acetone filled condensor under a nitrogen atmosphere were placed 4-methoxyphenol (Aldrich, 3.5 g) and methyl acrylate (Aldrich, 907 g, 10.5 mol). Methylamine (Aldrich, 163 g, 5.25 mol) was added slowly over about two hours through the gas inlet tube keeping the temperature less than about 30° C. After the addition was complete, the reaction mixture was stirred for 16 hours at ambient temperature. The excess methyl acrylate and much of the 1:1 addition product were then distilled from the reaction mixture under a vacuum of 3 mm Hg giving a final product purity of 96.6% the desired CH3N(CH2CH2CO2CH3)2.

Workup

  1. temperatureInto a 3 L round bottom flask cooled in a water bath
  2. customequipped with an overhead stirrer
  3. customthe temperature less than about 30° C
  4. additionAfter the addition
  5. distillationwere then distilled from the reaction mixture under a vacuum of 3 mm Hg

Sources & evidence

ORD record
ord-68f6c1fb248f438fb40fff0354f28081
Source dataset
uspto-grants-2013_09
Patent number
US08535559B2

Reaction notes

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