Water → N-[(1-{6-[(tert-Butylamino)(phenyl)methyl]pyridin-2-yl}-2-naphthyl)methyl]-2-methylaniline

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Reaction Steps

A mixture of 2.00 g (5.68 mmol) of 6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde, 1.24 g (17.0 mmol) of tert-butylamine, 40 g of molecular sieves (4A) in 40 ml of THF was stirred overnight at room temperature. Further on, the molecular sieves were separated, washed with 2×25 ml of THF, and the resulting solution was additionally centrifuged to split off some precipitate. This solution was evaporated to dryness. A solution of the residue in 40 ml of THF was cooled to −80° C., and 23.0 ml (17.3 mmol) of 0.75 M PhLi in ether was added. The resulting mixture was heated to room temperature for 1 h, and then 10 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 2×20 ml of ether. The combined organic extract was washed by 10 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: ethyl acetate-triethylamine=20:1, vol.). Yield 1.08 g (39%) of white solid as a ca. 1 to 1 mixture of two diastereomers. Anal. calc. for C34H35N3: C, 84.08; H, 7.26; N, 8.65. Found: C, 84.26; H, 7.39; N, 8.49. For 1H NMR (in CDCl3) see FIG. 3—Bottom spectrum.

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