Methylacrylamide → 3-[(3,5-dimethoxyphenyl)methylamino]-N-methyl-propanamide

HRID 2234401Notes

Reaction equation

HRID 2234401 reaction equation
[CH3:1][NH:2][C:3](=[O:6])[CH:4]=[CH2:5].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[CH2:12][NH2:13]>C(O)C>[CH3:18][O:17][C:15]1[CH:14]=[C:11]([CH2:12][NH:13][CH2:5][CH2:4][C:3]([NH:2][CH3:1])=[O:6])[CH:10]=[C:9]([O:8][CH3:7])[CH:16]=1

Participants

4

Reactant 2

HCID 14471MethylacrylamideHCID 420973(3,5-Dimethoxyphenyl)methanamine

Product 1

HCID 618606733-[(3,5-dimethoxyphenyl)methylamino]-N-methyl-propanamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

N-methylacrylamide (ABCR; 500 mg, 5.87 mmol) and 3,5-dimethoxybenzylamine (Aldrich; 0.98 mL, 6.46 mmol) were dissolved in ethanol (4 mL) and heated in a microwave at 140° C. for 45 minutes. The mixture was poured onto a 20 g SCX-2 column, washed with methanol and eluted with 3.5N NH3 in methanol. The product fractions were evaporated to the title compound as a yellow oil (1.3 g, 88%).

Workup

  1. additionThe mixture was poured onto a 20 g SCX-2 column
  2. washwashed with methanol
  3. washeluted with 3.5N NH3 in methanol
  4. customThe product fractions were evaporated to the title compound as a yellow oil (1.3 g, 88%)

Sources & evidence

ORD record
ord-1c1ae45c65f64fcd8a1df57615ec9650
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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