Methyl Acrylate → HCID 12469800, compound

HRID 2102869Notes

Reaction equation

HRID 2102869 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:8]([O:12][CH3:13])(=[O:11])[CH:9]=[CH2:10]>CO>[CH3:13][O:12][C:8](=[O:11])[CH2:9][CH2:10][NH:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 166581-Aminopiperidine

Product 1

HCID 12469800HCID 12469800, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-aminopiperidine (100 g, 1.00 mol) in dry methanol at 0° C., methyl acrylate (99.0 ml, 1.10 mol) was added dropwise. The resulting mixture was stirred at room temperature overnight. After evaporation of the solvent, heptane was added to the residue, and the white solid (impurity) removed by filtration. The filtrate was concentrated to dryness to afford 80.0 g (43%) of the title compound as a yellow oil. Alternatively this reaction was performed at 50° C. using toluene as the solvent with a 0.7 molar excess of 1-aminopiperidine. Excess 1-aminopiperidine was removed from the residue by co-distillation with xylene, then toluene and then hexane.

Workup

  1. customAfter evaporation of the solvent, heptane
  2. additionwas added to the residue
  3. customthe white solid (impurity) removed by filtration
  4. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-231cddd701f143b397239c70c662c0af
Source dataset
uspto-grants-2009_08
Patent number
US07576095B2

Reaction notes

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