Methyl Acrylate → methyl 3-(benzylamino)propanoate

HRID 1815819Notes

Reaction equation

HRID 1815819 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][CH3:14])(=[O:12])[CH:10]=[CH2:11]>CO>[CH2:1]([NH:8][CH2:11][CH2:10][C:9]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 7504Benzylamine

Product 1

HCID 423871methyl 3-(benzylamino)propanoateYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 55 mL (0.50 mole) benzylamine in 250 mL methanol was cooled in an ice bath. A solution of 54 mL (0.60 mole) methyl acrylate in 50 mL methanol was added dropwise over 30 minutes. The reaction mixture was then allowed to warm gradually to room temperature. After about 96 hours the reaction mixture was concentrated under reduced pressure and the residue vacuum distilled to provide 74.6 gm (77%) of the desired compound in two fractions.

Workup

  1. concentrationAfter about 96 hours the reaction mixture was concentrated under reduced pressure
  2. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-cc6300293c864202a509893d458ff212
Source dataset
uspto-grants-2005_04
Patent number
US06881733B1

Reaction notes

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