Ethyl Methacrylate → Ethyl 3-(benzylamino)-2-methylpropanoate

HRID 358904Notes

Reaction equation

HRID 358904 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:7]([O:6][C:1]([CH:2]([CH3:4])[CH2:3][NH:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:8]

Participants

4

Reactant 2

HCID 7343Ethyl Methacrylate2×HCID 7504Benzylamine

Product 1

HCID 13555213Ethyl 3-(benzylamino)-2-methylpropanoateYield 31.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

350 ml (2.8 moles) of ethyl methacrylate were added to a solution of 150 g (1.4 moles) of benzylamine dissolved in 400 ml of ethanol. The mixture was heated under reflux for 4 hours, and then 175 ml (1.4 mole) of ethyl methacrylate were added to it, after which it was heated under reflux for 24 hours. The solvent and the unreacted materials were then removed from the mixture by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with a 1:1 by volume mixture of ethyl acetate and toluene, to afford 98.0 g of N-(2-ethoxycarbonylpropyl)benzylamine as a red oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperatureafter which it was heated
  4. temperatureunder reflux for 24 hours
  5. customThe solvent and the unreacted materials were then removed from the mixture by evaporation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel
  7. washeluted with a 1:1 by volume mixture of ethyl acetate and toluene

Sources & evidence

ORD record
ord-2a2d6606e3034e8fa3b4c92c76fd275d
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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