Acetic Acid → HCID 28978254, compound

Participants

Reaction Steps

A solution of 2-iodoaniline (1.0 g, 4.57 mmol) in 15 mL 1,2-dichloroethane was treated with 1-methylpiperidin-4-one (530 μL, 4.57 mmol) followed by sodium triacetoxyborohydride (1.55 g, 7.31 mmol) then acetic acid (259 μL). The suspension was stirred at room temperature for 21 hours. After this time, the mixture was cooled to 0° C., quenched with 20 mL 1N NaOH and extracted with 2×100 mL CH2Cl2. The combined organic layer was dried over MgSO4, filtered and concentrated. The residue was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A light yellow oil was obtained (579 mg, 40.2%). 1H-NMR (CDCl3) δ 7.64 (dd, J=1.2, 8.1 Hz, 1H), 7.21-7.15 (m, 1H), 6.57 (d, J=8.1 Hz, 1H), 6.44-6.39 (m, 1H), 4.12-4.10 (m, 1H), 3.37-3.35 (m, 1H), 3.79-2.75 (m, 2H), 2.31 (s, 3H), 2.22-2.03 (m, 4H), 1.65-1.53 (m, 2H). MS (ESI): 317.1 (M+1, 100%).

Provenance & Evidence