Potassium sodium tartarate → (5-Aminomethyl-2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-phenyl)-methanol

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Reaction Steps

To a cold (0° C.) mixture of LiAlH4 (195 mg, 5.12 mmol) in dry THF (6 mL) was added 2-{[bis-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester (0.22 g, 0.55 mmol) as a solution in THF (5 mL). The resultant mixture was stirred at room temperature for 5 hours then cooled in an ice water bath. The mixture was treated with saturated aqueous sodium-potassium tartrate (11 mL) and diluted with THF (11 mL). The phases were separated and the aqueous phase was extracted with THF (2×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (20:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica gel (1 mm plate, 50:1:1 CH2Cl2-MeOH—NH4OH) gave COMPOUND 385 (56 mg, 26%) as a white solid. 1H NMR (CDCl3) δ 2.12 (s, 6H), 3.72 (s, 4H), 3.82 (s, 2H), 3.89 (s, 2H), 4.25 (s, 2H), 6.54 (br s, 1H), 7.05 (dd, 2H, J=4.8, 7.5 Hz), 7.14-7.17 (m, 1H), 7.22-7.28 (m, 2H). 7.37 (d, 2H, J=7.2 Hz), 8.36 (d, 2H, J=3.6 Hz); 13C NMR (CDCl3) δ 18.57, 46.53, 57.74, 59.20, 63.53, 122.76, 126.35, 130.26, 132.06, 133.38, 135.74, 138.46, 142.44, 143.79, 146.51, 156.35; ES-MS m/z 377 (M+H). Anal. Calcd. for C23H28N4O.0.2H2O: C, 72.68; H, 7.53; N, 14.74. Found: C, 72.69; H, 7.52; N, 14.40.

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