Uses
3-Bromopiperidin-2,6-dione was in reaction with sodium saccharin to synthesize glutarimides derivatives to observe their activities against Ehrlich ascites carcinoma in Swiss albino mice.A thalidomide analog (I) was prepd. from 2,3-dihydro-3-thioxo-1H-isoindol-1-one and 3-Bromo-2,6-Piperidinedione.
Synthesis
A solution of piperidine-2,6-dione (2.00 g) and liquid bromine (2.82 g, 0.90 mL, 17.7 mmol) in chloroform (15 mL) was slowly added to a 48-mL pressure-resistant glass reaction vessel fitted with a Teflon screw cap. The reaction mixture was heated to 110 degrees F. and the reaction mixture was kept at this reaction temperature and stirred for 45 minutes, the progress of the reaction was monitored by gas chromatography, and at the end of the reaction the reaction mixture was concentrated directly under vacuum to remove the solvated reactant. The crude glutarimide was dissolved in acetone (5 mL) and then sodium azide (3.44 g, 53.1 mmol) was added to this mixture, the reaction mixture then turned blue-violet and the reaction mixture was stirred at room temperature for 24 hours. At the end of the reaction, the reaction mixture was directly separated and purified by silica gel column chromatography, eluting with n-hexane/ethyl acetate (1/1) to give 3-bromopiperidine-2,6-dione.
