Methylamine → 2,6-Diisopropyl-3-methylaminomethyl-4-(4-fluorophenyl)-5-pentyl-pyridine

Participants

Reaction Steps

Methylammonium chloride (37.99 mg, 0.563 mmol) was added to a stirred solution of methylamine in methanol (2M, 0.28 mL) under argon in an oven-dried round bottom flask equipped with a stir bar. Then sodium cyanoborohydride (4 eq., 10.60 mg, 0.169 mmol) was added and 2,6-diisopropyl-4-(4-fluorophenyl)-5-pentyl-3-pyridinecarboxaldehyde (Example 114, Step A) (100 mg, 0.281 mmol) was added as a solution in methanol (2 mL). The reaction was refluxed for 18 hours and then quenched with water. Concentration and addition of CH2Cl2 (25 mL) allowed washings with water (2×15 mL), brine (1×25 mL), following which the solution was dried with MgSO4, filtered, and concentrated to afford a clear oil. Flash chromatography using silica gel (40% ether/CH2Cl2) yielded the title compound as a white solid (21 mg, 0.057 mmol, 20%). 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 4 H), 3.26 (m, 4 H), 2.24 (m, 5 H), 1.20 (m, 19 H), 0.783 (t, J=6.6 Hz, 3 H). FAB-MS: calcd for (C24H35FN2) 370, found 371 (M+H). mp 77-79° C. Rf=0.2 (20% ether/CH2Cl2).

Provenance & Evidence