Ethylamine → Ethyl N-ethyl-beta-alaninate

HRID 2207073Notes

Reaction equation

HRID 2207073 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]([O:8][CH2:9][CH3:10])(=[O:7])[CH:5]=[CH2:6]>CCO>[CH2:1]([NH:3][CH2:6][CH2:5][C:4]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 8821Ethyl Acrylate

Product 1

HCID 90223Ethyl N-ethyl-beta-alaninate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of ethylamine (70% in water, 5.8 mL) in EtOH (30 mL) was added to a suspension of ethyl acrylate (2.0 g) in EtOH (20 mL) at 0° C. and the mixture was stirred at RT for 30 mins. The mixture was concentrated under reduced pressure. The residue was purified by flash column chromatography on amino silica gel to afford the sub-title compound (2.4 g) as a pale yellow oil; 1H NMR (300 MHz, CDCl3); 4.13 (2H, q), 2.88 (2H, t), 2.66 (2H, q), 2.52 (2H, t), 1.24 (2H, t), 1.11 (3H, t).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash column chromatography on amino silica gel

Sources & evidence

ORD record
ord-63ae941d97b6425eaead5f2e79cfb7af
Source dataset
uspto-grants-2016_06
Patent number
US09376398B2

Reaction notes

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