Tert-Butylamine → HCID 71290277, compound

Participants

Reaction Steps

A mixture of 2.68 g (8.43 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde, 3.07 g (42.1 mmol) of tert-butylamine and 800 mg (12.7 mmol) of NaBH3CN and 100 ml of dry ethanol was stirred overnight at room temperature. The resulting mixture was evaporated to dryness, and the product was isolated by flash chromatography on silica gel 60 (40-63 um; ethyl acetate-triethylamine=20:1, vol.). Yield 1.61 g (51%) of white solid. Anal. calc. for C25H33N3: C, 79.95; H, 8.86; N, 11.19. Found: C, 80.11; H, 8.95; N, 10.95. 1H NMR (CDCl3): 8.87 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.83 (m, 1H, 8-H in naphthyl), 7.77 (m, 1H, 4-H in Py), 7.63 (d, J=8.6 Hz, 1H, 3-H in naphthyl), 7.46 (m, 1H, 3-H in Py), 7.41 (m, 1H, 7-H in naphthyl), 7.31-7.34 (m, 2H, 5,6-H in naphthyl), 7.27 (m, 1H, 5-H in Py), 3.97 (m, 2H, NaphCH2N), 3.53 (s, 21-1, PyCH2N), 1.17 (s, 9H, PyCH2NHtBu), 0.96 (s, 9H, NaphCH2NH′Bu).

Provenance & Evidence