Diisopropylaniline → HCID 66795703, compound

Participants

Reaction Steps

A mixture of 4.80 g (15.0 mmol) of 6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde and 2.70 g (15.0 mmol) of 2,6-diisopropylaniline in 50 ml of dry ethanol was refluxed overnight. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 5.50 g (76%) of orange oil which crystallized at room temperature. Anal. calc. for C33H39N3: C, 82.97; H, 8.23; N, 8.80. Found: C, 83.10; H, 8.41; N, 8.68. 1H NMR (CDCl3): 8.41 (m, 1H, 3-H in Py), 8.38 (s, 1H, CH═N), 8.00 (m, 1H, 4-H in Py), 7.91 (d, J=8.6 Hz, 4-H in naphthyl), 7.88 (m, 1H, 8-H in naphthyl), 7.66 (d, J=8.6 Hz, 3-H in naphthyl), 7.56 (m, 1H, 5-H in Py), 7.37-7.47 (m, 3H, 5,6,7-H in naphthyl), 7.10-7.18 (m, 3H, 3,4,5-H in Ph), 3.60 (m, 2H, CH2N), 3.02 (sept, J=6.8 Hz, 2H, CHMe2), 1.18 (d, J=6.8 Hz, 6H, CHMeMe′), 1.19 (d, J=6.8 Hz, 6H, CHMeMe′), 0.95 (s, 9H, tBu).

Provenance & Evidence