N,N-dimethyl-1-(4-methyl-1H-indol-3-yl)methanamine

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

Procedure: Dimethyl-(4-methyl-1H-indol-3-ylmethyl)-amine (20 g, 98 mmol) is suspended in acetonitrile, and warmed to completely dissolve the material. The reaction is cooled to room temperature and then methyl iodide (9.1 mL, 147 mmol) is added dropwise to the reaction. The reaction is covered with foil and then stirred at room temperature overnight. The reaction is then filtered and the filtrate evaporate in vacuo to give an oil that is taken up in acetonitrile. The white solid is then triturated with acetonitrile and ether, and combined with the original solid to give the title compound that is used without further purification (30 g, 87 mmol, 88%) LC/MS (M++1): 347. warmed to completely dissolve the material The reaction is then filtered the filtrate evaporate in vacuo to give an oil that The white solid is then triturated with acetonitrile and ether

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

Procedure: Dimethyl-(4-methyl-1H-indol-3-ylmethyl)-amine (20 g, 98 mmol) is suspended in acetonitrile, and warmed to completely dissolve the material. The reaction is cooled to room temperature and then methyl iodide (9.1 mL, 147 mmol) is added dropwise to the reaction. The reaction is covered with foil and then stirred at room temperature overnight. The reaction is then filtered and the filtrate evaporate in vacuo to give an oil that is taken up in acetonitrile. The white solid is then triturated with acetonitrile and ether, and combined with the original solid to give the title compound that is used without further purification (30 g, 87 mmol, 88%) LC/MS (M++1): 347. warmed to completely dissolve the material The reaction is then filtered the filtrate evaporate in vacuo to give an oil that The white solid is then triturated with acetonitrile and ether

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

Procedure: To a chilled solution of dimethyl amine (30 mL, 40% in water, 120 mmol) and formalin (13 mL, 37% in water, 84 mmol) in glacial acetic acid (30 mL) is added 4-methyl indole (21 g, 165 mmol) at 0° C. The reaction is warmed to room temperature and stirred for 3 hours. The reaction mixture is brought to pH 12 by addition of 50% NaOH and ice, and the product extracted with methylene chloride. The organic layers are dried over Na2SO4 filtered and evaporated in vacuo to give the title compound that is used without further purification (33 g, 162 mmol, 98%) LC/MS (M++1): 205.7. the product extracted with methylene chloride The organic layers are dried over Na2SO4 filtered evaporated in vacuo

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

Procedure: Dimethyl-(4-methyl-1H-indol-3-ylmethyl)-amine (20 g, 98 mmol) is suspended in acetonitrile, and warmed to completely dissolve the material. The reaction is cooled to room temperature and then methyl iodide (9.1 mL, 147 mmol) is added dropwise to the reaction. The reaction is covered with foil and then stirred at room temperature overnight. The reaction is then filtered and the filtrate evaporate in vacuo to give an oil that is taken up in acetonitrile. The white solid is then triturated with acetonitrile and ether, and combined with the original solid to give the title compound that is used without further purification (30 g, 87 mmol, 88%) LC/MS (M++1): 347. warmed to completely dissolve the material The reaction is then filtered the filtrate evaporate in vacuo to give an oil that The white solid is then triturated with acetonitrile and ether

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

Procedure: To a chilled solution of dimethyl amine (30 mL, 40% in water, 120 mmol) and formalin (13 mL, 37% in water, 84 mmol) in glacial acetic acid (30 mL) is added 4-methyl indole (21 g, 165 mmol) at 0° C. The reaction is warmed to room temperature and stirred for 3 hours. The reaction mixture is brought to pH 12 by addition of 50% NaOH and ice, and the product extracted with methylene chloride. The organic layers are dried over Na2SO4 filtered and evaporated in vacuo to give the title compound that is used without further purification (33 g, 162 mmol, 98%) LC/MS (M++1): 205.7. the product extracted with methylene chloride The organic layers are dried over Na2SO4 filtered evaporated in vacuo