Methyl Acrylate → Methyl 3-[(3-pyridinylmethyl)amino]propanoate

HRID 977959Notes

Reaction equation

HRID 977959 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][CH2:11][CH2:10][C:9]([O:13][CH3:14])=[O:12])[CH:2]=1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 310183-Pyridinemethanamine

Product 1

HCID 13606577Methyl 3-[(3-pyridinylmethyl)amino]propanoateYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Pyridylmethylamine (10.81 g) is dissolved in methanol (50 ml), and thereto is added dropwise methyl acrylate (8.60 g) under ice-cooling. The mixture is stirred at room temperature for 18 hours. The mixture is distilled to remove the solvent, and then the residue is distilled under reduced pressure to give methyl 3-(3-pyridylmethylamino)propionate (16.02 g, 82.5%), b.p. 119°-120° C./0.4 mmHg.

Workup

  1. temperaturecooling
  2. distillationThe mixture is distilled
  3. customto remove the solvent
  4. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-1acc470bba7d43b78a2489f231ba991c
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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