Phthalimide → N-[3-(4-Pyridyl)propyl]phthalimide

Participants

Reaction Steps

Cool a mixture of phthalimide (5.4 g, 37 mmol) and PPh3 (9.6 g, 37 mmol) in tetrahydrofuran (80 mL) to 0° C. Add dropwise a solution of 4-pyridine propanol (5.0 g, 37 mmol) and diethyl azodicarboxylate (5.8 mL, 37 mmol) in tetrahydrofuran (55 mL). After 2 hours warming to room temperature, concentrate the reaction mixture to a brown paste and perform flash-chromatography on silica gel eluting with 20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH) solution in methylene chloride to afford 2-(3-pyridin-4-yl-propyl)isoindole-1,3-dione as a yellow solid. TLC (SiO2): Rf=0.68 [20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH solution in methylene chloride].

Provenance & Evidence