Methyl Acrylate → Methyl N-benzyl-N-(3-methoxy-3-oxopropyl)-beta-alaninate

HRID 1410546Notes

Reaction equation

HRID 1410546 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH2:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH3:6][O:5][C:1]([CH2:2][CH2:3][N:14]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])=[O:4]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 7504Benzylamine

Product 1

HCID 69926Methyl N-benzyl-N-(3-methoxy-3-oxopropyl)-beta-alaninateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

At room temperature, to a 500 mL three-necked bottle, 18.9 g (0.22 mol) of methyl acrylate and 100 mL of methanol were added, and a mixture solution of 10.7 g (0.1 mol) of benzylamine and 50 mL of methanol was slowly added dropwise to the three-necked bottle under stirring. The temperature was naturally elevated, and the addition rate was controlled so that the temperature of reaction system was not greater than 50° C. After the addition, the reaction was stirred at room temperature for 0.5 h, and reacted for 8 h under reflux. After completion of the reaction, the unreacted methanol and methyl acrylate were removed by vacuum distillation to obtain light yellow oily product N,N-bis(β-methoxy carbonylethyl)benzylamine, 27.3 g, yield 98%, by 174-176° C./533 Pa.

Workup

  1. customthe addition rate was controlled so that the temperature of reaction system
  2. customwas not greater than 50° C
  3. additionAfter the addition
  4. stirringthe reaction was stirred at room temperature for 0.5 h
  5. customreacted for 8 h
  6. temperatureunder reflux
  7. customAfter completion of the reaction
  8. customthe unreacted methanol and methyl acrylate were removed by vacuum distillation

Sources & evidence

ORD record
ord-6e0738b6f89a4a4489a8b4eb9d23dda3
Source dataset
uspto-grants-2014_12
Patent number
US08921563B2

Reaction notes

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