N-[2-(1H-indol-4-yl)ethyl]-N-propylpropan-1-amine

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

Procedure: N-chlorosuccinimide (2.52 g, 18.9 mmol) was added to a solution of 4-[2-(dipropylamino)ethyl]indole (IV) (3 g, 12.28 mmol) in toluene (10 mL) and was stirred at room temperature for 1 h. The resultant mixture was washed with an aqueous solution of NaOH 5% and then an aqueous solution of HCl 1N (30 mL) was added to the organic layer and was heated at reflux temperature for 1 h. When the mixture reached room temperature, the organic layer was separated and the aqueous layer was basified with an aqueous solution of NaOH and extracted with AcOEt. The organic layer was dried, filtered and concentrated to obtain 2.1 g (66%) of 4-[2-(dipropylamino)ethyl]indol-2-one (I), which was purified and converted into its hydrochloride salt. The resultant mixture was washed with an aqueous solution of NaOH 5% an aqueous solution of HCl 1N (30 mL) was added to the organic layer was heated at reflux temperature for 1 h reached room temperature the organic layer was separated extracted with AcOEt The organic layer was dried filtered concentrated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of pyridinium tribromide 90% (8.72 g, 24.5 mmol) in acetic acid 50% (50 mL) was added to a solution of 4-[2-(dipropylamino)ethyl]indol (IV) (5 g, 20.5 mmol) in acetic acid 50% (100 mL) and was stirred at 50° C. for 3 h. When the resultant mixture reached room temperature, it was stirred at this temperature for 16 h. The reaction mixture was concentrated to obtain an aqueous residue, which was diluted with water (100 mL), basified with an aqueous solution of NaOH 10% and extracted with AcOEt. The organic layer was dried, filtered and concentrated to obtain 4.3 g (81%) of 4-[2-(dipropylamino)ethyl]indol-2-one (I). reached room temperature it was stirred at this temperature for 16 h The reaction mixture was concentrated to obtain an aqueous residue, which extracted with AcOEt The organic layer was dried filtered concentrated

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

Procedure: A mixture of 4-[(2-amino)ethyl]indole (III) (2.0 g, 12.48 mmol), 1-iodopropane (8.5 g, 50 mmol), NaHCO3 (2.3 g, 27.4 mmol) in toluene (40 mL) was stirred at reflux temperature for 21 h. NaHCO3 (1.15 g, 13.7 mmol) in water (20 mL) and 1-iodopropane (2.12 g, 12.47 mmol) were added to the resultant mixture and was stirred at the same temperature for 6 h. When the mixture reached room temperature, it was filtered and layers were separated. The organic layer was washed with water (15 mL), dried, filtered and evaporated to obtain 2.53 g (83%) of 4-[2-(dipropylamino)ethyl]indole (IV). at reflux temperature for 21 h was stirred at the same temperature for 6 h reached room temperature it was filtered layers were separated The organic layer was washed with water (15 mL) dried filtered evaporated