6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → HCID 19974622, compound

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Reaction Steps

A solution of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (15.63 g) and 2-bromo-4'-nitroacetophenone (16.47 g) in a mixture of ethanol (150 ml) and methylene chloride (150 ml) was heated at 60° for 24 hours. After cooling to room temperature yellow crystals appeared. These were collected by filtration and dried in vacuo to give the title compound (9.4 g); MP: 216°. NMR(D6 -DMSO) includes signals at d 3.6(6H,s,2×OCH3); 4.2(2H,s,N--CH2 --Ph); 4.95(2H,s,CO--CH2 --N); 6.6(2H,aromatics isoquinoline); 8(4H,m,aromatics).

Provenance & Evidence