Trimethylsilyl isocyanate → HCID 23289845, compound

Participants

Reaction Steps

4-(8-Chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-yl)-1-(4-piperidine-acetyl)piperazine (270 mg, 0.591 mmol) was added to anhydrous CH2Cl2 (2.7 ml). TMSNCO (320 mg, 0.37 ml, 2.36 mmol) was added by syringe. The mixture was stirred at room temperature for 90 hours and then quenched with saturated NaHCO3. More water and CH2Cl2 were added, and the mixture was shaken and separated. The aqueous phase was extracted with CH2Cl2 (4×20 ml), and the combined organic phases were washed with brine, dried (Na2SO4), decanted and concentrated. The crude residue was purified by flash chromatography (5%MeOH/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH) and the pure product was obtained (295 mg, 66%) MS (FAB, M+H)=529.

Provenance & Evidence