2-[3-(dimethylamino)propoxy]-5-methylaniline

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

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

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, cooled (about 0° C.) solution of 2-(3-dimethylamino-propoxy)-5-methyl-phenylamine (208 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (140 μL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, amino pyrazine (95 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. After stirring for 4 hours, the reaction was cooled to room temperature and stirred for 8 hours. The precipitate that formed was filtered, rinsed with toluene (2×1 mL), and dried under reduced pressure (35% yield). After stirring for 4 hours the reaction was cooled to room temperature stirred for 8 hours The precipitate that formed was filtered rinsed with toluene (2×1 mL) dried under reduced pressure (35% yield)

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

Procedure: To a stirred solution of [2-(3-dimethylamino-propoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester (617 mg, 2.0 mmol) in 5 mL of dioxane was added hydrochloric acid (2 mL; 4N in dioxane). After stirring for 12 hours, the reaction was diluted with 20 ml of 1N hydrochloric acid and washed with ethyl acetate (2×30 mL). The aqueous layer was basified with 10% aqueous sodium carbonate (50 mL) and extracted with ethyl acetate (3×50 mL). The ethyl acetate was washed with brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced to yield the corresponding aniline. washed with ethyl acetate (2×30 mL) extracted with ethyl acetate (3×50 mL) The ethyl acetate was washed with brine (1×30 mL) dried (MgSO4) filtered The filtered solution was concentrated

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, cooled (about 0° C.) solution of 2-(3-dimethylamino-propoxy)-5-methyl-phenylamine (208 mg, 1.0 mmol) in toluene (3.0 mL) was added triethylamine (140 μL, 1.0 mmol) and triphosgene (98 mg, 0.33 mmol). After stirring for 30 minutes, amino pyrazine (95 mg, 1.0 mmol) was added and the reaction was heated to 65 degrees C. After stirring for 4 hours, the reaction was cooled to room temperature and stirred for 8 hours. The precipitate that formed was filtered, rinsed with toluene (2×1mL), and dried under reduced pressure (35% yield). After stirring for 4 hours the reaction was cooled to room temperature stirred for 8 hours The precipitate that formed was filtered rinsed with toluene (2×1mL) dried under reduced pressure (35% yield)

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

Procedure: To a stirred solution of [2-(3-dimethylamino-propoxy)-5-methyl-phenyl]-carbamic acid tert-butyl ester (617 mg, 2.0 mmol) in 5 mL of dioxane was added hydrochloric acid (2 mL; 4N in dioxane). After stirring for 12 hours, the reaction was diluted with 20 mL of 1N hydrochloric acid and washed with ethyl acetate (2×30 mL). The aqueous layer was basified with 10% aqueous sodium carbonate (50 mL) and extracted with ethyl acetate (3×50 mL). The ethyl acetate was washed with brine (1×30 mL), there dried (MgSO4), and filtered. The filtered solution was concentrated under reduced to yield the corresponding aniline. washed with ethyl acetate (2×30 mL) extracted with ethyl acetate (3×50 mL) The ethyl acetate was washed with brine (1×30 mL), there dried (MgSO4) filtered The filtered solution was concentrated