Potassium Carbonate → HCID 86621289, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-bromopropyl)-3-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.61 g, 1.56 mmol) was dissolved in 5 mL of DMF along with 430 mg (3.1 mmol) of potassium carbonate and 0.32 g (1.56 mol) of tert-butyl piperidin-4-ylcarbamate. The solution was heated to 70° C. for 16 hours then poured in water. The solution was extracted 2× with ethyl acetate and the water layer discarded. The combined organic phase was washed 3 times with brine, then dried (MgSO4) and concentrated. The residue was subjected to Biotage chromatography (10-50% ethyl acetate-hexane) to afford 0.45 g (55%) of tert-butyl (1-{3-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]propyl}piperidin-4-yl)carbamate. MS (ES) m/z 505.1; HPLC purity 97.9% at 210-370 nm, 10.5 min.; Xterra RP18, 3.5 u, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Bicarb Buff.Ph=9.5/ACN+MeOH) for 10 min, hold 4 min.

Provenance & Evidence