Methyl iodide → 2-(Cyclohexylmethylamino)ethanol

To a mixture of N-cyclohexylethanolamine (2.1 g, 14.7 mmol) and tetrahydrofuran (70 ml) were added iodomethane (1.1 ml, 17.6 mmol) and triethylamine (2.26 ml, 16.2 mmol) at room temperature, and the reaction mixture was stirred for 1 hour under heating refluxing. The reaction mixture was cooled at room temperature (external temperature). To the mixture was added water to stop the reaction. To the reaction mixture was added ethyl acetate, and the organic layer was separated. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate, NH silica gel) to obtain the title compound (790.7 mg, 5.0 mmol, 34%).

1. temperatureunder heating
2. temperaturerefluxing
3. customthe reaction
4. customthe organic layer was separated
5. washThe organic layer was washed with water
6. distillationan aqueous saturated sodium chloride solution, and the solvent was distilled off under reduced pressure
7. customThe residue was purified by silica gel chromatography (ethyl acetate, NH silica gel)

ORD record

ord-915546486de84b18951beee6183c3d2f

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2