2-(3,4-dimethoxyphenyl)-1-(isopropylamino)ethane

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in an rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in an rotatory evaporator

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-isopropylethylamine (2.4 g, 11 mmol) and 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-bromoethane (3.04 g, 10 mmol) were dissolved in DMF and, thereafter, potassium iodide (1.61 g, 11 mmol) and anhydrous potassium carbonate (1.5 g, 10 mmol) were added and the mixture was stirred at 80-90° C. for 1 h; thereafter, ice water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g). extraction The extracted organic layer was dried with magnesium sulfate the solvent was evaporated the resulting residue was purified The fractions containing the product were collected the solvent was evaporated

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-isopropylethylamine (2.4 g, 11 mmol) and 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-bromoethane (3.04 g, 10 mmol) were dissolved in DMF and, thereafter, potassium iodide (1.61 g, 11 mmol) and anhydrous potassium carbonate (1.5 g, 10 mmol) were added and the mixture was stirred at 80-90° C. for 1 h; thereafter, ice water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g). extraction The extracted organic layer was dried with magnesium sulfate the solvent was evaporated the resulting residue was purified The fractions containing the product were collected the solvent was evaporated

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction-mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in a rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in a rotatory evaporator

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in an rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in an rotatory evaporator

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in an rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in an rotatory evaporator

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(3,4-Dimethoxyphenyl)-N-isopropylethylamine (2.4 g, 11 mmol) and 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-bromoethane (3.04 g, 10 mmol) were dissolved in DMF and, thereafter, potassium iodide (1.61 g, 11 mmol) and anhydrous potassium carbonate (1.5 g, 10 mmol) were added and the mixture was stirred at 80-90° C. for 1 h; thereafter, ice water was added and extraction was conducted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was evaporated; the resulting residue was purified by being subjected to column chromatography on silica gel using a 7:3:1 solvent system of cyclohexane, ethyl acetate and methanol as an eluent. The fractions containing the product were collected and the solvent was evaporated to yield the end compound 1-[4-nitro-2-(1H-pyrrol-1-yl)phenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-isopropylamino]ethane (0.9 g). extraction The extracted organic layer was dried with magnesium sulfate the solvent was evaporated the resulting residue was purified The fractions containing the product were collected the solvent was evaporated

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction-mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in a rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in a rotatory evaporator

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

Procedure: In a sulfuration-flask, there is added while stirring 20 ml of 20% aqueous sodium hydroxide to 22,3 g of N-(3,4-dimethoxyphenylethyl)-N-isopropyl amine. The reaction mixture is then cooled in CO2 alcohol-cooling-bath to a temperature of -10° to -15°, to which is then added dropwise, while stirring a solution of 14.7 g of dichloroacetylchloride in 10 ml toluene. After everything has been added, the cooling-bath is removed and the reaction mixture is stirred for another 2 hours until it reaches room-temperature. It is then poured into an ice/water mixture and the organic material is extracted with toluene. The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate and concentrated in an rotatory evaporator. The title product is thus obtained as viscous oil in a yield of 28.4 g. In a sulfuration-flask, there is added to which is then added dropwise After everything has been added the cooling-bath is removed It is then poured into an ice/water mixture the organic material is extracted with toluene The toluene extracts are washed once with diluted sodium hydroxide and with diluted hydrochloric acid and twice with water dried over sodium sulfate concentrated in an rotatory evaporator