1,2,3,4-Tetrahydroisoquinoline → Benzamide, N-(1,2,3,4-tetrahydro-2-propylisoquinolin-5-yl)-3,4,5-trimethoxy-

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Reaction Steps

5-Amino-2-n-propyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (13.7 g) prepared as in Example 5 was suspended in dry benzene (100 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 3,4,5-trimethoxybenzoyl chloride was dissolved in dry benzene (100 ml) and this solution was added to the solution of the tetrahydroisoquinoline. The mixture was refluxed for 5 days. The precipitate formed was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining solid (11.7 g) was purified by recrystallization from ethanol to yield 5-(3,4,5-trimethoxybenzamido)-2-n-propyl-1,2,3,4-tetrahydroisoquinoline as a white powder, m.p., 158.5°-159.5° C.

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