2-[cyclohexyl(methyl)amino]ethanol

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl-N-methyl-2-aminoethanol (25 g) is added dropwise to thionyl chloride (120 cc) and then the mixture is heated for 24 hours at 70° C. After the excess thionyl chloride has been distilled off, the orange oil obtained is stirred into ethyl ether (200 cc) to give a white solid, which is separated off by filtrattion and then washed with ether. 2-(N-Cyclohexyl-N-methyl-amino)-1-chloroethane (30 g) is obtained in the form of a white solid melting at 154° C. After the excess thionyl chloride has been distilled off the orange oil obtained to give a white solid, which is separated off by filtrattion washed with ether

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%). After the reaction mixture was cooled at 0° C. (external temperature) the reaction mixture was stirred at 60° C. for 1 hour was added the reaction the organic layer was separated After the organic layer was washed with water an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%). under heating refluxing the reaction the organic layer was separated The organic layer was washed with water 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)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Cyclohexyl-N-methyl-2-aminoethanol (25 g) is added dropwise to thionyl chloride (120 cc) and then the mixture is heated for 24 hours at 70° C. After the excess thionyl chloride has been distilled off, the orange oil obtained is stirred into ethyl ether (200 cc) to give a white solid, which is separated off by filtrattion and then washed with ether. 2-(N-Cyclohexyl-N-methyl-amino)-1-chloroethane (30 g) is obtained in the form of a white solid melting at 154° C. After the excess thionyl chloride has been distilled off the orange oil obtained to give a white solid, which is separated off by filtrattion washed with ether

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of sodium hydride (50%, 241 mg, 5.0 mmol) and tetrahydrofuran (20 ml) was added 2-[cyclohexyl(methyl)amino]ethanol (791 mg, 5.0 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 60° C. for 30 minutes. After the reaction mixture was cooled at 0° C. (external temperature), to the reaction mixture was added dropwise a solution of tributyl-iodomethyl-tin (2.2 g, 5.0 mmol) in tetrahydrofuran (5 ml), and the reaction mixture was stirred at 60° C. for 1 hour. After the reaction mixture was cooled at room temperature (external temperature), water was added to stop the reaction. Ethyl acetate was added to the reaction mixture, and the organic layer was separated. After the organic layer was washed with water, an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel) to obtain the title compound (790.7 mg, 4.3 mmol, 85%). After the reaction mixture was cooled at 0° C. (external temperature) the reaction mixture was stirred at 60° C. for 1 hour was added the reaction the organic layer was separated After the organic layer was washed with water an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure The residue was purified by silica gel chromatography (heptane:ethyl acetate=20:1, NH silica gel)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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%). under heating refluxing the reaction the organic layer was separated The organic layer was washed with water 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)