Ethyl N-benzyl-N-methyl-beta-alaninate → Ethyl 3-(methylamino)propanoate

HRID 555896Notes

Reaction equation

HRID 555896 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])C1C=CC=CC=1>C(O)C.[Pd]>[CH3:1][NH:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 1

HCID 15147383Ethyl N-benzyl-N-methyl-beta-alaninate

Product 1

HCID 541480Ethyl 3-(methylamino)propanoateYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-(benzyl(methyl)amino)propanoate (3 g, 13.56 mmol) in ethanol (67.8 mL) was added palladium, 10 wt. % on carbon (0.3 g, 0.282 mmol) and hydrogenated (double-walled balloon pressure) at room temperature for 3 h. The reaction mixture was filtered via a pad of Celite, and the filtrate was concentrated in vacuo to give ethyl 3-(methylamino)propanoate (1.12 g, 63.0% yield) as a light golden yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered via a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c97739bc5bfd44178aec7a5f4b68c6b2
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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