Ammonia → HCID 20605024, compound

Participants

Reaction Steps

A solution of 1,2,3,4-tetrahydroquinoline (1.0 mL, 7.94 mmol) in 20 mL 1,2-dichloroethane was treated with 1-methylpiperidin-4-one (2.76 mL, 23.8 mmol) followed by sodium triacetoxyborohydride (8.4 g, 39.7 mmol) then acetic acid (2.25 mL). The suspension was stirred at room temperature for 1 day. After this time, the mixture was cooled to 0° C., quenched with 5 mL 1N NaOH and stirred for 20 minutes. The suspension was extracted with 100 mL CH2Cl2. The organic layer was dried over MgSO4, filtered and concentrated to give a light residue which was subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 then 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (440 mg, 24.1%). 1H-NMR (CDCl3) δ: 7.07-7.02 (m, 1H), 6.95 (d, J=7.5 Hz, 1H), 6.65 (d, J=8.4 Hz, 1H), 6.55 (pseudo t, J=7.8 Hz, 1H), 3.65-3.55 (m, 1H), 3.20 (t, J=5.7 Hz, 2H), 2.99-2.95 (m, 2H), 2.73 (t, J=6.0 Hz, 2H), 2.31 (s, 3H), 2.11-2.05 (m, 2H), 1.93-1.73 (m, 6H).

Provenance & Evidence