3-[2-(dimethylamino)ethoxy]-4-methylaniline

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 9 (0.25 g, 1.29 mmol) and 5 (0.29 ml, 1.44 mmol) in EtOH (8 mL) were added 2 drops of conc. HCl. The mixture was heated under reflux overnight. After cooling to room temperature, EtOH was removed under reduced pressure. The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) and the aquous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, the solids were filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc) to yield the title compound as a light yellow solid (0.25 g). The mixture was heated under reflux overnight EtOH was removed under reduced pressure The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) the aquous layer was extracted with EtOAc (2×50 mL) The combined organic layers were dried over MgSO4 the solids were filtered the filtrate was concentrated under reduced pressure The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc)

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

Procedure: A solution of 8 (1.15 g) in 6N HCl (10 mL) was heated at 60° C. for 4 hours. After cooling to room temperature, the solution was neutralized with 6N NaOH solution. The aqueous mixture was extracted with EtOAc (2×30 mL), the combined organic layers were washed with brine (1×50 mL) and dried over MgSO4. The solids were filtered, and the filtrate was concentrated under reduced pressure to give the desired product as an oil (0.68 g). The aqueous mixture was extracted with EtOAc (2×30 mL) the combined organic layers were washed with brine (1×50 mL) dried over MgSO4 The solids were filtered the filtrate was concentrated under reduced pressure

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

Procedure: To a solution of 9 (0.25 g, 1.29 mmol) and 5 (0.29 ml, 1.44 mmol) in EtOH (8 mL) were added 2 drops of conc. HCl. The mixture was heated under reflux overnight. After cooling to room temperature, EtOH was removed under reduced pressure. The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) and the aquous layer was extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, the solids were filtered, and the filtrate was concentrated under reduced pressure. The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc) to yield the title compound as a light yellow solid (0.25 g). The mixture was heated under reflux overnight EtOH was removed under reduced pressure The residue was partitioned between sat. NaHCO3 (aq.) and EtOAc (100 mL each) the aquous layer was extracted with EtOAc (2×50 mL) The combined organic layers were dried over MgSO4 the solids were filtered the filtrate was concentrated under reduced pressure The residue was purified on Florisil® (50% EtOAc/Hexanes to 15% MeOH/EtOAc)

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

Procedure: A solution of 8 (1.15 g) in 6N HCl (10 mL) was heated at 60° C. for 4 hours. After cooling to room temperature, the solution was neutralized with 6N NaOH solution. The aqueous mixture was extracted with EtOAc (2×30 mL), the combined organic layers were washed with brine (1×50 mL) and dried over MgSO4. The solids were filtered, and the filtrate was concentrated under reduced pressure to give the desired product as an oil (0.68 g). The aqueous mixture was extracted with EtOAc (2×30 mL) the combined organic layers were washed with brine (1×50 mL) dried over MgSO4 The solids were filtered the filtrate was concentrated under reduced pressure