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

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Reaction Steps

5-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (12.9 g) prepared as in Example 4 was dissolved in dry benzene (100 ml) and 0.5 g of 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. A precipitate formed immediately and the mixture was refluxed for 1 hour. The precipitate was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining residue was recrystallized from ethanol to yield 12.0 g of the desired product as a white powder, m.p. 160°-161.5° C.

Provenance & Evidence