Triphosgene → HCID 22490380, compound

Participants

Reaction Steps

To a stirred solution of N-(3,4-difluoro-phenyl)-N′-[4-(4-iodo-phenyl)-1-methyl-piperidin-4-ylmethyl]-ethane-1,2-diamine (0.36 g, 1.0 mmol) in THF (10 mL) at 0° C. was added TEA (0.91 mL, 6.5 mmol, 6.5 eq.) and triphosgene (0.195 g, 0.65 mmol, 0.65 eq.). The mixture was stirred at room temperature for 4 h, diluted with EtOAc (25 mL) and washed with saturated brine (2×25 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation to give a yellow oil. The crude product was purified by flash column chromatography by eluting with 2% MeOH/CH2Cl2 to give 1-(3,4-difluoro-phenyl)-3-[4-(4-iodo-phenyl)-1-methyl-piperidin-4-ylmethyl]-imidazolid in-2-one (0.023 g, 0.045 mmol, 5%) as a pale foam. MS (ESI): 512.1/513.1 (M+H), impurity peak 690.9/692.0.

Provenance & Evidence