4-(1H-indol-3-yl)butan-2-one

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 4-(1H-indol-3-yl)-butan-2-one (1.0 g, 5.3 mmol) in methanol (20 mL is added ammonium acetate (4.45 g, 57.73 mmol) and sodium cyanoborohydride (0.37 g, 5.9 mmol) at room temperature. The resulting mixture is allowed to stir for 64 hours at the same temperature. The reaction mixture is quenched by addition of 1 N hydrochloric acid and adjusted to pH ˜2. The mixture is concentrated and extracted with dichloromethane (50 mL). Then the aqueous phase is adjusted to pH ˜12 using 4 N aqueous sodium hydroxide and extracted with dichloromethane (3×50 mL). The combined organic phases are dried with sodium sulfate and concentrated in vacuo. The resulting residue is subjected to flash column chromatography (5%-30% methanol in dichloromethane) to afford 3-(1H-indol-3-yl)-1-methyl-propylamine (622 mg, 62%) as an oil. The reaction mixture is quenched by addition of 1 N hydrochloric acid The mixture is concentrated extracted with dichloromethane (50 mL) extracted with dichloromethane (3×50 mL) The combined organic phases are dried with sodium sulfate concentrated in vacuo

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

Procedure: To a solution of 4-(1H-indol-3-yl)-butan-2-one (1.0 g, 5.3 mmol) in methanol (20 mL is added ammonium acetate (4.45 g, 57.73 mmol) and sodium cyanoborohydride (0.37 g, 5.9 mmol) at room temperature. The resulting mixture is allowed to stir for 64 hours at the same temperature. The reaction mixture is quenched by addition of 1 N hydrochloric acid and adjusted to pH ˜2. The mixture is concentrated and extracted with dichloromethane (50 mL). Then the aqueous phase is adjusted to pH ˜12 using 4 N aqueous sodium hydroxide and extracted with dichloromethane (3×50 mL). The combined organic phases are dried with sodium sulfate and concentrated in vacuo. The resulting residue is subjected to flash column chromatography (5%-30% methanol in dichloromethane) to afford 3-(1H-indol-3-yl)-1-methyl-propylamine (622 mg, 62%) as an oil. The reaction mixture is quenched by addition of 1 N hydrochloric acid The mixture is concentrated extracted with dichloromethane (50 mL) extracted with dichloromethane (3×50 mL) The combined organic phases are dried with sodium sulfate concentrated in vacuo

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

Procedure: To a solution of 4-(1H-indol-3-yl)-butan-2-one (1.0 g, 5.3 mmol) in methanol (20 mL is added ammonium acetate (4.45 g, 57.73 mmol) and sodium cyanoborohydride (0.37 g, 5.9 mmol) at room temperature. The resulting mixture is allowed to stir for 64 hours at the same temperature. The reaction mixture is quenched by addition of 1 N hydrochloric acid and adjusted to pH ˜2. The mixture is concentrated and extracted with dichloromethane (50 mL). Then the aqueous phase is adjusted to pH ˜12 using 4 N aqueous sodium hydroxide and extracted with dichloromethane (3×50 mL). The combined organic phases are dried with sodium sulfate and concentrated in vacuo. The resulting residue is subjected to flash column chromatography (5%-30% methanol in dichloromethane) to afford 3-(1H-indol-3-yl)-1-methyl-propylamine (622 mg, 62%) as an oil. The reaction mixture is quenched by addition of 1 N hydrochloric acid The mixture is concentrated extracted with dichloromethane (50 mL) extracted with dichloromethane (3×50 mL) The combined organic phases are dried with sodium sulfate concentrated in vacuo