Water → 3-(5-chloro-1H-indol-3-yl)propan-1-amine

Participants

Reaction Steps

To a solution of 3-(3-Azidopropyl)-5-chloro-1H-indole (0.299 g; 1.27 mmol) in THF (9 mL) were added triphenylphosphine (0.354 g; 1.34 mmol) and water (0.6 mL). The reaction mixture was stirred at room temperature for 22 hours and was then concentrated under reduced pressure. The residue was dissolved in dichloromethane (10 mL) and 10 mL of 6N hydrochloric acid were added. After separation, the aqueous layer was further extracted with dichloromethane (2×10 mL) and the pH was adjusted to 14 with an aqueous solution of sodium hydroxide 6N. This basic solution was extracted dichloromethane (3×20 mL) and the combined organic layer was dried over magnesium sulphate, and evaporated to afford 0.089 g (34%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-amine as a white solid.

Provenance & Evidence