1-Heptanamine → 2-bromo-n-heptylacetamide
Reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Br:9][CH2:10][C:11](Br)=[O:12]>C1COCC1>[Br:9][CH2:10][C:11]([NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of n-heptylamine (2.30 g, 20 mmol) in THF (20 ml) was dropped a solution of bromoacetyl bromide (2.02 g, 10 mmol) in THF (10 ml) with ice-cooling and stirring and the mixture was stirred at 0° C. for 1 hour. The reaction solution was concentrated in vacuo, water was added to the residue and the mixture was extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom to provide 2.36 g (yield 99%) of crude 2-bromo-N-heptylacetamide as oil.
Workup
- temperaturecooling
- stirringthe mixture was stirred at 0° C. for 1 hour
- concentrationThe reaction solution was concentrated in vacuo, water
- additionwas added to the residue
- extractionthe mixture was extracted with ether
- washThe organic layer was washed with water
- dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-a7664e5a95d24c09b0a5613e119d3f86
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06969711B2
Reaction notes
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