Potassium Carbonate → HCID 59708791, compound

Participants

Reaction Steps

Compound 10 (3.30 g, 9.30 mmol) was added slowly to a stirred suspension of potassium carbonate (4.10 g, 29.7 mmol) in acetone (120 mL). After 0.5 hour, iodobutyrate (4.0 mL, 29.60 mmol) was added and the reaction was stirred at reflux for 14 hours. The reaction mixture was concentrated to dryness and the residue was taken up in water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic extracts were successively washed with water and brine, dried over anhydrous sodium sulfate and concentrated to an oil. Purification by column chromatography (silica gel, dichloromethane, then 95:5 dichloromethane/methanol, v/v) gave 11 (3.27 g, 91%) as an orange oil: 1H NMR (500 MHz, CDCl3) δ 1.62-1.71 (m, 4H), 3.11-3.17 (m, 5H), 2.39-3.41 (m, 2H), 3.48-3.77 (m, 4H), 7.83-7.91 (m, 4H), 9.33 (br, 2H), 11.54 (br, 1H); ESI MS m/z 288 [C16H21N3O2+H]+.

Provenance & Evidence