Sodium hydride → HCID 68714062, compound

Participants

Reaction Steps

To a solution of (1,3-dimethylpiperidin-3-yl)methanol (0.50 g, 3.5 mmol) in dry DMF (10 mL) at room temperature, 60% sodium hydride in oil (0.28 g, 7.0 mmol) was added. The reaction mixture was stirred at room temperature for 5 minutes and 3-fluoro benzonitrile (0.44 g, 3.7 mmol) was added. Due to excessive foaming the reaction mixture was diluted with dry DMF to 15 mL. The reaction mixture was then stirred at room temperature over night and quenched with water. The product was extracted with EtOAc and the organic layer was dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography using a gradient with EtOAc:MeOH:TEA (1:0.1:0.05) in EtOAc, which gave the product as a colorless oil. Yield: 0.53 g (59%). 1H NMR (400 MHz, CD3OD) δ 7.41 (t, 1H, J=8.11 Hz), 7.20-7.27 (m, 3H), 3.89 (d, 1H, J=8.89 Hz), 3.82 (d, 1H, J=8.89 Hz), 2.21-2.51 (m, 3H), 2.19 (s, 3H), 2.12 (m, 1H), 1.54-1.67 (m, 3H), 1.21-1.30 (m, 1H), 1.07 (s, 3H).

Provenance & Evidence