5-Methoxytryptamine → Melatonin

Participants

Reaction Steps

To a suspension, cooled in ice, of 20 g (0.105 moles) of pure 5-methoxytryptamine in 400 ml methylene chloride there is slowly added, under stirring, a cold solution of 20 ml (0.21 moles) of acetic anhydride in 200 ml methylene chloride. Stirring and cooling are continued for 1 hour (the reaction progression can be controlled by TCL) so as to obtain a full solution; then the solution is washed with Na2CO3 ×2, under long stirring, and then with water. The organic phase, dried on Na2SO4 and evaporated, provides 24 g (yield 98%) of lightly colored melatonine.

Provenance & Evidence