2-Methylpiperidine → 5-Bromo-2-(2-methylpiperidin-1-YL)benzaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 5-bromo-2-fluorobenzaldehyde (13.20 g; 65.02 mmol) in DMSO (160 mL) and water (40 mL) were added 2-methylpiperidine (15.35 mL; 130.04 mmol) and anhydrous sodium carbonate (13.78 g; 130.04 mmol). The resulting mixture was heated at 120° C. for 16 h after which it was allowed to cool to RT. Reaction mixture was partitioned between H2O and Et2O and the combined organic layers were washed with brine (pH 5-6 adjusted with HCl), dried over MgSO4, filtered and dried under vacuum to give the title compound as a brown yellow oil (16.3 g, 89%). 1H NMR (CDCl3, 300 MHz) δ 10.40 (s, 1H), 7.93 (d, J=2.5 Hz, 1H), 7.62 (dd, J=8.6, 2.5 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 3.17 (m, 1H), 3.06 (m, 1H), 2.81 (ddd, J=11.7, 7.6, 3.9 Hz, 1H), 1.89 (m, 1H), 1.83-1.65 (m, 3H), 1.58-1.42 (m, 2H), 0.91 (d, J=6.3 Hz, 3H). HPLC (Method A): Rt 2.20 min (Purity: 93.7%). LC/MS (Method B): 282.1 (M+H)+.

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