Phthalimide → 2-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

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 3-pyridine propanol (5.0 g, 37 mmol) and diethyl azodicarboxylate (5.8 mL, 37 mmol) in tetrahydrofuran (50 mL). After 2 hours, dilute the reaction mixture with methylene chloride (100 mL), and water (100 mL). Wash the organic layer with water (100 mL), then brine (100 mL). Dry over magnesium sulfate, filter and concentrate to afford 2-(3-pyridin-3-yl-propyl)isoindole-1,3-dione as a yellow solid which can be used without further purification.

Provenance & Evidence