Methanol → N-((1-(6-((2,6-Diisopropylphenylamino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

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Reaction Steps

Methanol (30 mL), toluene (10 mL), and compound 6b (2.11 g, 3.91 mmol) were heated to reflux under nitrogen. Formic acid (95%) (5 drops) was added followed by portions of NaBH3CN (0.983 g, 15.6 mmoL). The borohydride was added in four portions over an hour. After 3 hours at reflux the yellow color of the imine had faded completely and the volatiles were removed by evaporation on a rotary evaporator. Water (20 mL) and Et2O (30 mL) were added, and the organics were separated and dried over brine. The ether solution was then dried over MgSO4, filtered, and evaporated to give the diamine 7o as a pale pink solid. Yield: 2.1 g, 99%. 1H NMR (500 MHz, CD2-Cl2): 7.90 (t, 2H), 7.82 (t, 1H), 7.56 (d, 1H), 7.38-7.52 (m, 4H), 7.29 (d, 1H), 7.07 (d, 2H), 7.03 (m, 1H), 6.74 (s, 2H), 4.28 (m, 2H), 4.08 (br t, 1H), 3.96 (br, 2H), 3.45 (m, 1H), 3.33 sept, 2H), 2.19 (s, 3H), 2.05 (s, 6H), 1.15 (d, 12H).

Provenance & Evidence