2-Methoxyethylamine → 3-(benzyl(methyl)amino)-N-(2-methoxyethyl)propanamide

HRID 1408101Notes

Reaction equation

HRID 1408101 reaction equation
[CH2:1]([N:8]([CH3:15])[CH2:9][CH2:10][C:11]([O:13]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18][CH2:19][NH2:20]>>[CH2:1]([N:8]([CH3:15])[CH2:9][CH2:10][C:11]([NH:20][CH2:19][CH2:18][O:17][CH3:16])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 824679Methyl 3-(benzyl(methyl)amino)propanoate

Product 1

HCID 665868063-(benzyl(methyl)amino)-N-(2-methoxyethyl)propanamideYield 61%

Conditions

Temperature
100 °C

Procedure

To methyl 3-(benzyl(methyl)amino)propanoate (1.5 g, 7.24 mmol, 1.00 equiv) was added 2-methoxyethanamine (11 g, 146.45 mmol, 20.00 equiv) and the mixture was stirred for 2 days at 100° C. in sealed tube. The resulting mixture was concentrated under vacuum and purified via silica gel chromatography (dichloromethane/methanol 30:1) to afford 1.1 g (61%) of the product as a yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. custompurified via silica gel chromatography (dichloromethane/methanol 30:1)

Sources & evidence

ORD record
ord-f2472b8d6caf4edab09942d6c83696e3
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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