Sodium Hydroxide → 5-Chlorotryptamine

Participants

Reaction Conditions

Reaction Steps

Cool to 5° C., a suspension of LiAlH4 (40.97 g) in THF (700 ml). Add a solution of AlCl3 (53.9 g, 0.40 mole) to THF (645 ml) over about 30 minutes while maintaining the temperature at about 5° C. and 10° C. Add (2-(5-chloro-1H-Indol-3-yl)-2-oxo-acetamide (20 g, 0.09 mole) in THF (900 ml) while maintaining the temperature at between 5° C. and 7.5° C. When the addition is complete warm to room temperature. Stir overnight and then cool to 7° C. and slowly add a solution of NaOH 50% (342 g, 4.28 mol). After stirring for about 1 hour, add anhydrous Na2SO4 (30 g) and filter the suspension on a celite bed. Evaporate the filtrate to dryness to give an oil. Combine the and Et2O (500 mL) and add a solution of Et2O/HCl 4.5N (15 mL) at room temperature to give a solid. Stir the suspension at room temperature for 1 hour, filter, and wash with 50 mL Et2O, dry under vacuum at 50° C. to give the hydrochloride of the title compound.

Provenance & Evidence