Diisopropylethylamine → N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine

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Reaction Steps

A suspension of 6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (1.25 g, 6.00 mmol), bromoacetyl chloride (0.75 mL, 9.01 mmol), and polymer supported diisopropylethylamine (4.7 g, 18 mmol) was stirred for 4 hours, filtered, and taken to a residue under reduced pressure. The residue was redissolved in 2.0M methylamine in tetrahydrofuran (15 mL) and stirred overnight. The solution was concentrated under reduced pressure and purified by column chromatography to afford N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine as a mixture of apparent rotameric forms in DMSO (0.90 g, 3.07 mmol).

Provenance & Evidence