Acetic Acid → N-[(6-Bromopyridin-2-yl)methyl]-2,6-bis(1-ethylpropyl)aniline

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Reaction Steps

In argon atmosphere, a mixture of 11.2 g (28 mmol) of N-[(1E)-(6-bromopyridin-2-yl)methylene]-2,6-bis(1-ethylpropyl)aniline, 2.80 g (45 mmol) of NaBH3CN, 1 ml of AcOH and 230 ml of methanol was refluxed for 12 h. The obtained mixture was cooled, poured into 300 ml of water, and then crude product was extracted with 3×200 ml of ethyl acetate. The combined extract was dried over Na2SO4 and evaporated to dryness. Yield 10.3 g (93%) of yellow oil. Anal. calc. for C23H31BrN2: C, 65.50; H, 7.75; N, 6.94. Found: C, 65.36; H, 7.69; N, 6.82. 1H NMR (CDCl3): δ 7.52 (m, 1H, 4-H in Py), 7.41 (m, 1H, 3-H in Py), 7.38 (m, 1H, 5-H in Py), 7.03-7.08 (m, 1H, 4-H in dipentylphenyl), 6.97-6.99 (m, 2H, 3, 5-H in dipentylphenyl), 4.10 (s, 2H, CH2NH), 3.73 (br.s, 1H, NH), 2.86 (m, 2H, CHEt2), 1.70 (m, 4H, CH2Me), 1.49 (m, 4H, CH2Me), 0.79 (t, J=7.3 Hz, 12H, CH2Me).

Provenance & Evidence