2-(2-Ethoxy-phenoxy)-ethylamine

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

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: To a solution of 1-acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (300 mg) and 2-(2-ethoxyphenoxy)ethylamine (391 mg) in dioxane (4 ml) were added potassium iodide (17 mg) and 18-crown-6 (26 mg), and the mixture was reacted in a sealed tube at 180° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent to give 111 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino] propyl]indoline-7-carbonitrile as an oil. the mixture was reacted in a sealed tube at 180° C. for 18 hours The reaction mixture was concentrated under reduced pressure the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent

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

Procedure: To a solution of 1-acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (300 mg) and 2-(2-ethoxyphenoxy)ethylamine (391 mg) in dioxane (4 ml) were added potassium iodide (17 mg) and 18-crown-6 (26 mg), and the mixture was reacted in a sealed tube at 180° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent to give 111 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino] propyl]indoline-7-carbonitrile as an oil. the mixture was reacted in a sealed tube at 180° C. for 18 hours The reaction mixture was concentrated under reduced pressure the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent

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

Procedure: A mixture of [(3-bromopropyl)sulfonyl]benzene (26.3 g, 100 mmol), 2-(2-ethoxyphenoxy)ethanamine (18.1 g, 100 mmol), and potassium carbonate (55.3 g, 400 mmol) in 200 mL of methyl ethyl ketone is heated at reflux for 18 hours. The reaction mixture is cooled, filtered, and the filtrate is evaporated. The residue is dissolved in warm 2-propanol and treated with oxalic acid (9.3 g, 101 mmol). The precipitated salt is filtered and recrystallized from 2-propanol to yield 3.2 g (7%) of product, mp 184-188° C. is heated at reflux for 18 hours The reaction mixture is cooled filtered the filtrate is evaporated The residue is dissolved in warm 2-propanol The precipitated salt is filtered recrystallized from 2-propanol

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

Procedure: A mixture of [(3-bromopropyl)sulfonyl]benzene (26.3 g, 100 mmol), 2-(2-ethoxyphenoxy)ethanamine (18.1 g, 100 mmol), and potassium carbonate (55.3 g, 400 mmol) in 200 mL of methyl ethyl ketone is heated at reflux for 18 hours. The reaction mixture is cooled, filtered, and the filtrate is evaporated. The residue is dissolved in warm 2-propanol and treated with oxalic acid (9.3 g, 101 mmol). The precipitated salt is filtered and recrystallized from 2-propanol to yield 3.2 g (7%) of product, mp 184-188° C. is heated at reflux for 18 hours The reaction mixture is cooled filtered the filtrate is evaporated The residue is dissolved in warm 2-propanol The precipitated salt is filtered recrystallized from 2-propanol

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

Procedure: A mixture of 1.9 g of 1-chloro-3-(4-fluorophenoxy)-propane, l.8 g of 2-(2-ethoxyphenoxy)ethylamine, 0.53 g of sodium carbonate and 60 ml of dimethylformamide was heated at 80°-90° C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride, M.P. 78°-82° C. Recrystallization from ethanol-benzene gave white crystals, M.P. 84°-86° C. After cooling extracted with benzene The extract was washed with water dried over sodium sulfate evaporated under reduced pressure The oily residue was dissolved in ether treated with ethanolic hydrogen chloride under cooling The precipitate was collected by filtration dried

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

Procedure: A mixture of 1.9 g of 1-chloro-3-(4-fluorophenoxy)-propane, l.8 g of 2-(2-ethoxyphenoxy)ethylamine, 0.53 g of sodium carbonate and 60 ml of dimethylformamide was heated at 80°-90° C for 15 hours. After cooling, the reaction mixture was poured into water and extracted with benzene. The extract was washed with water and dried over sodium sulfate and evaporated under reduced pressure. The oily residue was dissolved in ether and treated with ethanolic hydrogen chloride under cooling. The precipitate was collected by filtration and dried to give N-{2-(2-ethoxyphenoxy)ethyl}-3-(4-fluorophenoxy)propylamine hydrochloride, M.P. 78°-82° C. Recrystallization from ethanol-benzene gave white crystals, M.P. 84°-86° C. After cooling extracted with benzene The extract was washed with water dried over sodium sulfate evaporated under reduced pressure The oily residue was dissolved in ether treated with ethanolic hydrogen chloride under cooling The precipitate was collected by filtration dried

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

Procedure: To a solution of 1-acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (300 mg) and 2-(2-ethoxyphenoxy)ethylamine (391 mg) in dioxane (4 ml) were added potassium iodide (17 mg) and 18-crown-6 (26 mg), and the mixture was reacted in a sealed tube at 180° C. for 18 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent to give 111 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino] propyl]indoline-7-carbonitrile as an oil. the mixture was reacted in a sealed tube at 180° C. for 18 hours The reaction mixture was concentrated under reduced pressure the residue was purified by flash column chromatography on silica gel using a mixture of methylene chloride and methanol (40/1) as eluent

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

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