1-Hydroxybenzotriazole → N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-bromo-2,4-dimethoxybenzamide

Participants

Reaction Steps

5-Bromo-2,4-dimethoxybenzoic acid (0.296 g, 1.1 mmol), 1-(3-dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (0.186 g, 0.94 mmol) and 1-hydroxybenzotriazole (0.144 g, 0.94 mmol) were dissolved in dry DMF (10 ml) and stirred at room temperature under argon for 25 mins before 5-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.153 g, 0.94 mmol) was added. The mixture was then stirred overnight under argon at room temperature. The DMF was removed in vacuo and the residue taken up into ethyl acethate and washed with water. The organic layer was dried over magnesium sulfate, concentrated in vacuo and the residue recrystallised from ethyl acethate/hexane to afford the title compound as a solid (0.106 g)

Provenance & Evidence