Trifluoroacetic acid → 2,6-Diisopropyl-N-((6-(2-((phenylamino)methyl)phenyl)pyridin-2-yl)methyl)aniline

Participants

Reaction Steps

Methanol (40 mL) and (E)-tert-butyl 2-(6-((2,6-diisopropylphenylimino)methyl)pyridin-2-yl)benzyl(phenyl)carbamate (12) (2.56 g (4.67 mmol) were combined to form a yellow suspension. Then some NaBH3CN (0.293 g, 4.66 mmol) was added followed by four drops of 88% formic acid. Then additional NaBH3CN (0.878 g, 14.0 mmol) was added in small portions over 5 minutes. The mixture was heated to reflux for 3 hours then evaporated to near dryness. Water (20 mL) and Et2O (40 mL) were then added followed by a CH2Cl2 (6 mL). The organics were separated, dried over brine then magnesium sulfate, filtered, and evaporated to a thick oil. Chloroform (25 mL) was then added to form a solution. Trifluoroacetic acid (10 mL) was added and the mixture was heated to reflux to cause gas evolution. After 45 minutes the mixture was cooled to ambient temperature and 3 M NaOH (60 mL) was added. The biphasic mixture was rapidly stirred for several minutes. The organics were separated, washed with water (50 mL) and brine (5 mL). The organics were then separated and dried over magnesium sulfate. Filtration and evaporation afforded the product as a thick oil that was dried thoroughly under reduced pressure at 65° C. Yield: 2.0 g, 95%). 1H NMR (CD2Cl2, 500 MHz): 7.77 (t, 1H), 7.39-7.58 (m, 5H), 7.31 (d, 1H), 7.02-7.12 (m, 5H), 6.63 (t, 1H), 6.58 (d, 2H), 4.62 (br, 1H), 4.41 (br, 2H), 4.23 (br, 1H), 3.97 (br, 1H), 3.35 (sept, 2H), 1.20 (d, 12H).

Provenance & Evidence