Methylacrylamide → 3-(Sec-butylamino)-N-methylpropanamide
Reaction equation
[CH3:1][NH:2][C:3](=[O:6])[CH:4]=[CH2:5].[CH:7]([NH2:11])([CH2:9][CH3:10])[CH3:8]>C(O)C>[CH3:8][CH:7]([NH:11][CH2:5][CH2:4][C:3]([NH:2][CH3:1])=[O:6])[CH2:9][CH3:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of N-methylacrylamide (ABCR; 500 mg, 5.87 mmol), sec-butylamine (Aldrich; 530 mL, 5.22 mmol) and ethanol (4 mL) was heated in a microwave to 140° C. for 45 minutes and then at 150° C. for 30 minutes. The reaction mixture was cooled and poured onto an SCX-2 cartridge (5 g) and cartridge washed through with methanol (˜50 mL). Products were then eluted with 2M ammonia in methanol (˜50 mL) and evaporated to afford the title compound as a straw coloured oil (563 mg; 61%)
Workup
- temperatureThe reaction mixture was cooled
- additionpoured onto an SCX-2 cartridge (5 g) and cartridge
- washwashed through with methanol (˜50 mL)
- washProducts were then eluted with 2M ammonia in methanol (˜50 mL)
- customevaporated
Sources & evidence
- ORD record
- ord-f376d88a2dd4488192f61fa516534766
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709471B2
Reaction notes
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