N-bromobutanimide → HCID 59807044, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(2-(pyrrolidin-1-yl)ethyl)-1,2,3,4-tetrahydroquinoline (490 mg, 2.13 mmol) in 10 mL of carbontetrachloride was cooled to 0° C. then treated with NBS (378 mg, 2.13 mmol) portionwise. The resulting suspension was stirred at 0° C. for 3.5 hours. The mixture was filtered through celite and the filter pad was rinsed with 3×20 mL hexanes. The filtrate was concentrated to give a light brown residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2 to give a light brown oil (380 mg, 57.7%). 1H-NMR (CDCl3) δ: 7.09 (dd, J=2.4, 8.7 Hz, 1H), 7.02 (d, J=2.4 Hz, 1H), 6.46 (d, J=8.7 Hz, 1H), 3.42 (t, J=7.8 Hz, 2H), 3.29 (t, J=5.7 Hz, 2H), 2.76-2.55 (m, 8H), 1.95-1.89 (m, 2H), 1.82-1.77 (m, 4H).

Provenance & Evidence