Aniline → N-Isopropylaniline

A mixture of aniline (0.46 mls, 5 mmol) and cesium hydroxide (0.61 mls, 15 mmol) was stirred at 25° C. for 30 mins in DMF (25 mls). 2-iodopropane (2.5 mls, 25 mmol) was added dropwise over 5 mins, the reaction was heated to 30° C. and stirred for 16 hours. The solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with CH2Cl2 and the combined organic layer was washed with water and then brine and was dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc to provide the intermediate 4a (55 mg, 4 mmol, 81.4% yield) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 7.11-7.02 (t, J=7.9 Hz, 2H), 6.63-6.54 (t, J=7.3 Hz, 2H), 6.54-6.45 (d, J=7.8 Hz, 1H), 3.60-3.45 (hept, J=6.3 Hz, 1H), 3.41-3.25 (s, 1H), 1.14-1.06 (d, J=6.3 Hz, 6H).