Triethylamine → N-cycloheptyl-N-methylamine
Reaction equation
[C:1]1(=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CN.[CH2:12]([N:14](CC)CC)C>ClCCCl>[CH3:12][NH:14][CH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 1,2-dichloroethane (50 ml) were suspended cycloheptanone (2 g), methylamine hydrochloride (3 g) and triethylamine (6.2 ml), and to the suspension was added sodium triacetoxy boron hydride (5.3 g) under ice-cooling. Under nitrogen atmosphere, the mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was neutralized with sodium hydroxide. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give N-methylcycloheptylamine (1.8 g) as colorless oil.
Workup
- temperaturecooling
- customThe solvent was evaporated
- extractionThe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated sodium chloride solution
- dry with materialdried with anhydrous magnesium sulfate
- customUnder reduced pressure, the solvent was evaporated
Sources & evidence
- ORD record
- ord-12d8481317424c4ebfe61a82c32b5ab0
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06268354B1
Reaction notes
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