Hydrochloric Acid → HCID 18669078, compound

Participants

Reaction Steps

Potassium hydroxide (320 mg) was added to a solution of ethyl 4-{3-[5-chloro-2-(4-chlorophenyl)-1H-indol-3-yl]-1-oxopropyl}piperazine-1-acetate (Example 109, 350 mg, 0.72 mmol) in methanol and the mixture was stirred at room temperature overnight. Water was added and the pH was adjusted to 7.0 with hydrochloric acid (2M). The mixture was extracted with ethyl acetate, the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was crystallised from ethyl acetate:methanol (99:1) to give the title compound as a pale solid (300 mg, 90%). 1H NMR (250 MHz, CD3OD) δ2.20-2.26 (2H, m), 2.92-2.97 (2H, m), 3.10-3.25 (4H, m), 3.55-3.60 (2H, m), 3.90-4.01 (4H, m), 7.10 (1H, dd, J 8.8, 2.0 Hz), 7.38 (1H, d, J 8.8 Hz), and 7.45-7.60 (5H, m). m/z (ES+) 460, 462 (M+1).

Provenance & Evidence