1,2,3,4-Tetrahydroisoquinoline → Benzamide, 2-chloro-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 (9.2 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 2-chlorobenzoyl chloride was dissolved in dry benzene (100 ml) and this solution was added to the solution of the tetrahydroisoquinoline. A white precipitate formed immediately and the mixture was then refluxed for 1 hour. The precipitate was collected by filtration and was washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining residue was recrystallized from ethanol to yield 12.6 g of the desired product as fluffly, crystalline plates, m.p., 189.5°-191.5° C.

Provenance & Evidence