Sodium Hydroxide → HCID 67492670, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-N-(1-methylpiperidin-4-yl)-N-phenylpropanamide (0.31 g, 0.953 mmol) was treated with anhydrous AlCl3 (0.5 g) and the resulting mixture was stirred at 185° C. for 2.5 h. The reaction was brought to room temperature, diluted with water (20 mL), then basified with 1 N NaOH solution (25 mL) and product was extracted into ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (MeOH:CH2Cl2, 5:95) to obtain 3-methyl-1-(1-methylpiperidin-4-yl)indolin-2-one (0.19 g, 82%) a solid. 1H NMR (DMSO-d6) δ: 1.31 (d, 3H, J=7.5 Hz), 1.50-1.58 (m, 2H), 1.99 (t, 2H, J=11.7 Hz), 2.20 (s, 3H), 2.32-2.42 (m, 2H), 2.84-2.90 (m, 2H), 3.44 (q, 1H), 3.99-4.10 (m, 1H), 7.00 (t, 1H, J=7.2 Hz), 7.12 (d, 1H, J=7.8 Hz), 7.23 (t, 1H, J=7.8 Hz), 7.30 (d, 1H, J=7.5 Hz); ESI-MS (m/z, %) 245 (MH+, 100).

Provenance & Evidence