Ethanol → 3-[(2-Methoxyethyl)amino]-N-methylpropanamide

HRID 2234409

Reaction equation

HRID 2234409 reaction equation
[CH3:1][NH:2][C:3](=[O:6])[CH:4]=[CH2:5].[CH3:7][O:8][CH2:9][CH2:10][NH2:11].CCO>CO>[CH3:7][O:8][CH2:9][CH2:10][NH:11][CH2:5][CH2:4][C:3]([NH:2][CH3:1])=[O:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 80182-MethoxyethylamineHCID 14471Methylacrylamide

Product 1

HCID 283071863-[(2-Methoxyethyl)amino]-N-methylpropanamideYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

N-Methylacrylamide (ABCR; 500 mg, 5.87 mmol), 2-Methoxyethylamine (Aldrich; 441 mg, 5.87 mmol), and EtOH (2 mL) were combined and heated in a microwave at 140° C. for 40 minutes. The reaction mixture was cooled and added to a 5 g SCX-2 column pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) then the product eluted with 2M ammonia in MeOH. Product containing fractions were evaporated in vacuo to give the title compound as a clear oil (608 mg, 65%)

Workup

  1. temperatureThe reaction mixture was cooled
  2. customflushed with MeOH (2 column volumes)
  3. washthe product eluted with 2M ammonia in MeOH
  4. additionProduct containing fractions
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-542e4945d87a4bf388dd5870b467d054
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Linked notes

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