Acetic Acid → HCID 13336314, compound

Participants

Reaction Steps

4-bromoaniline (1.0 g, 5.813 mmol) was dissolved in anhydrous dichloroethane (30 mL) in a dry argon purged flask fitted with a magnetic stir bar. 1-methylpiperidin-4-one (671 ul, 5.813 mmol), acetic acid (329 ul, 5.813 mmol) and sodium triacetoxyborohydride (1.848 g, 8.719 mmol) are added to the flask and mixture stirred at ambient temperature for 22 hours then heated to 55° C. for 4 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel and 1M sodium hydroxide solution added to adjust pH to 10. The organic layer was collected and the aqueous layer further extracted with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the crude purified via chromatography on silica gel (methanol:CH2Cl2, 5:95 then 2M NH3 in methanol:CH2Cl2, 1:9) to yield an off-white solid, 78 (1.0 g, 63.9%). 1H NMR (CDCl3) δ 1.40-1.58 (m, 2H), 1.98-2.22 (m, 4H), 2.31 (s, 3H), 2.73-2.89 (m, 2H), 3.15-3.32 (m, 1H), 3.45-3.58 (m, 1H), 6.47 (d, 2H, J=8.8 Hz), 7.23 (d, 2H, J=8.8 Hz); ESI-MS (m/z, %): 269/271 (MH+, 100%).

Provenance & Evidence