2-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol as produced in Example 4-(1) in an amount of 2 g (8.36 mmol) was added to methylene chloride (20 ml) and thionyl chloride (0.91 ml, 12.54 mmol) was slowly added dropwise at room temperature, followed by stirring for 24 h. Thereafter, the reaction mixture was subjected to extraction with methylene chloride and washed with a saturated solution of sodium bicarbonate, followed by drying with anhydrous magnesium sulfate and evaporation of the solvent to yield the end compound 1-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (2.15 g) was slowly added dropwise at room temperature Thereafter, the reaction mixture was subjected to extraction with methylene chloride washed with a saturated solution of sodium bicarbonate by drying with anhydrous magnesium sulfate and evaporation of the solvent

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

Procedure: A portion (0.50 g, 2.1 mmol) of the 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol produced in (1) above was dissolved in dimethyl sulfoxide (6 ml) and 60% sodium hydride (0.12 g, 3 mmol) was added to the resulting solution. The reaction mixture was stirred at room temperature for 1 h and 1-chloro-3,4-dinitrobenzene (0.48 ml, 4 mmol) was added on a water bath. The mixture was stirred at room temperature for 2 h and after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with chloroform. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 15:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end compound were collected and the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol to yield the titled compound 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (0.31 g). The mixture was stirred at room temperature for 2 h after adding a saturated aqueous solution of sodium bicarbonate, three extractions dried with sodium sulfate concentrated under vacuum The residue was purified the fractions containing the end compound were collected the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-methylethylamine (2.77 ml, 0.015 mol) and 2-bromoethanol (1.13 ml, 0.015 mol) were dissolved in N,N-dimethylformamide (10 ml). To the resulting solution, potassium iodide (2.45 g, 0.015 mol) was added, followed by stirring at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and, thereafter the solvent was evaporated under vacuum; after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with ethyl acetate. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 9:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end product were collected and the solvent was evaporated under vacuum, followed by drying to yield the end compound 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol (1.35 g) as an oil. The reaction mixture was cooled to room temperature the solvent was evaporated under vacuum after adding a saturated aqueous solution of sodium bicarbonate, three extractions dried with sodium sulfate concentrated under vacuum The residue was purified the fractions containing the end product were collected the solvent was evaporated under vacuum by drying

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-methylethylamine (2.77 ml, 0.015 mol) and 2-bromoethanol (1.13 ml, 0.015 mol) were dissolved in N,N-dimethylformamide (10 ml). To the resulting solution, potassium iodide (2.45 g, 0.015 mol) was added, followed by stirring at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and, thereafter the solvent was evaporated under vacuum; after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with ethyl acetate. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 9:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end product were collected and the solvent was evaporated under vacuum, followed by drying to yield the end compound 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol (1.35 g) as an oil. The reaction mixture was cooled to room temperature the solvent was evaporated under vacuum after adding a saturated aqueous solution of sodium bicarbonate, three extractions dried with sodium sulfate concentrated under vacuum The residue was purified the fractions containing the end product were collected the solvent was evaporated under vacuum by drying

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol as produced in Example 4-(1) in an amount of 2 g (8.36 mmol) was added to methylene chloride (20 ml) and thionyl chloride (0.91 ml, 12.54 mmol) was slowly added dropwise at room temperature, followed by stirring for 24 h. Thereafter, the reaction mixture was subjected to extraction with methylene chloride and washed with a saturated solution of sodium bicarbonate, followed by drying with anhydrous magnesium sulfate and evaporation of the solvent to yield the end compound 1-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (2.15 g) was slowly added dropwise at room temperature Thereafter, the reaction mixture was subjected to extraction with methylene chloride washed with a saturated solution of sodium bicarbonate by drying with anhydrous magnesium sulfate and evaporation of the solvent

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

Procedure: A portion (0.50 g, 2.1 mmol) of the 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol produced in (1) above was dissolved in dimethyl sulfoxide (6 ml) and 60% sodium hydride (0.12 g, 3 mmol) was added to the resulting solution. The reaction mixture was stirred at room temperature for 1 h and 1-chloro-3,4-dinitrobenzene (0.48 ml, 4 mmol) was added on a water bath. The mixture was stirred at room temperature for 2 h and after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with chloroform. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 15:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end compound were collected and the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol to yield the titled compound 1-(3,4-dinitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane hydrochloride (0.31 g). The mixture was stirred at room temperature for 2 h after adding a saturated aqueous solution of sodium bicarbonate, three extractions dried with sodium sulfate concentrated under vacuum The residue was purified the fractions containing the end compound were collected the solvent was evaporated under vacuum, with the residue being recrystallized from ethanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-methylethylamine (2.77 ml, 0.015 mol) and 2-bromoethanol (1.13 ml, 0.015 mol) were dissolved in N,N-dimethylformamide (10 ml). To the resulting solution, potassium iodide (2.45 g, 0.015 mol) was added, followed by stirring at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and, thereafter the solvent was evaporated under vacuum; after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with ethyl acetate. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 9:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end product were collected and the solvent was evaporated under vacuum, followed by drying to yield the end compound 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol (1.35 g) as an oil. The reaction mixture was cooled to room temperature the solvent was evaporated under vacuum after adding a saturated aqueous solution of sodium bicarbonate, three extractions dried with sodium sulfate concentrated under vacuum The residue was purified the fractions containing the end product were collected the solvent was evaporated under vacuum by drying