Phthalimide → HCID 66980463, compound

Participants

Reaction Conditions

Reaction Steps

The (1-benzyl-4-fluoropiperidin-4-yl)methyl methanesulfonate (1.82 g, 6.04 mmol, Preparation #V.1) was dissolved in DMF (18 mL) and isoindoline-1,3-dione (1.07 g, 7.25 mmol), Bu4NI (1.12 g, 3.02 mmol) and KOtBu (1.36 g, 12.1 mmol) were added. The resulting mixture was stirred at about 100° C. for about 12 h. The mixture was cooled to rt and concentrated under reduced pressure. The residue was diluted with water (10 mL) and extracted with Et2O (3×10 mL). The combined organic layers were washed with brine (2×20 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH/DCM to afford 2-((1-benzyl-4-fluoropiperidin-4-yl)methyl)isoindoline-1,3-dione (0.8 g, 38%): LC/MS (Table 2, Method f) Rt=2.21 min; MS m/z 353 (M+H)+.

Provenance & Evidence