Methyl Methacrylate → Methyl 2-methyl-3-[(phenylmethyl)amino]propanoate

HRID 2165111Notes

Reaction equation

HRID 2165111 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH3:7][O:6][C:1](=[O:5])[CH:2]([CH3:4])[CH2:3][NH:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6658Methyl MethacrylateHCID 7504Benzylamine

Product 1

HCID 97781Methyl 2-methyl-3-[(phenylmethyl)amino]propanoateYield 76.41%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl methacrylate (64.2 ml, 60.07 g, 0.6 mole) was added slowly at 0° C. (ice bath) to benzylamine (54.6 ml, 53.6 g, 0.5 mole) in 200 ml of methanol. The reaction solution was heated to reflux overnight. After being cooled, the solution was concentrated under vacuum to remove the excess of methyl methacrylate and methanol. Unreacted benzylamine was removed by heating the residue in a Kugelrohr oven under vacuum to yield the crude 3-phenylmethylamino-2-methyl-propanoic acid methyl ester (79.2 g, 76.41%).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux overnight
  3. temperatureAfter being cooled
  4. concentrationthe solution was concentrated under vacuum
  5. customto remove the excess of methyl methacrylate and methanol
  6. customwas removed
  7. temperatureby heating the residue in a Kugelrohr oven under vacuum

Sources & evidence

ORD record
ord-53f5928078bf4e728d15bb8b7ec558c0
Source dataset
uspto-grants-1990_07
Patent number
US04939161

Reaction notes

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