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

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Reaction Steps

5-Amino-2-n-propyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (10 g) prepared as in Example 5 was suspended in dry benzene (100 ml) and 0.5 g dry potassium bicarbonate was added. A 0.1 mole excess of 3,4-dimethoxybenzoyl 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 at the end of this period was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining solid was purified by recrystallization from ethanol to yield 6.7 g of 5-(3,4-dimethoxybenzamido)-2-n-propyl-1,2,3,4-tetrahydroisoquinoline as a white powder, m.p. 146°-147° C.

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