2-Benzyl-6-nitro-1,2,3,4-tetrahydroisoquinoline → HCID 15489611, compound

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Reaction Steps

A THF (184 mL) solution of compound (17) (4.6 g, 17 mmole) with platinum oxide (230 mg) was hydrogenated for 18 hrs. at 50 psi. The catalyst was filtered off and platinum oxide (230 mg) was added and the hydrogenation continued for 72 hrs. The completed hydrogenation was filtered to provide a THF solution of the intermediate, 2-benzyl-1,2,3,4-tetrahydroisoquinolin-6-yl amine (18). Triethylamine was added to the THF solution of (18) followed by the dropwise addition of 4'-trifluoromethylbiphenyl-2-carbonyl chloride (4.88 g., 17 mmole) from Example 3. The contents were stirred subsequently for 17 hrs. The solvent was removed under vacuum, water (50 mL) was added, the contents stirred for 3 hr., the product filtered off and dried under vacuum to yield 5.93 g (71%) of compound (19) as a white solid.

Provenance & Evidence