Synthesis
General method: 1,5-dibromopentane (11.9 mmol) was slowly added to a mixture of phthalimide potassium salt (1 g, 5.4 mmol) and anhydrous K2CO3 (0.82 g, 5.94 mmol) in acetone (15 mL). The reaction mixture was heated to 60-65 °C under argon protection and stirred for 6-10 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water (50 mL) was added to the residue and extracted with dichloromethane (30 mL x 3). The organic phases were combined, washed with saturated aqueous NaCl, dried over anhydrous Na2SO4 and filtered. The solvent was removed by concentration under reduced pressure. The crude product was purified by silica gel column chromatography with dichloromethane/acetone (50:1) as eluent to give N-(5-bromopentyl)phthalimide.
References
[1] Archiv der Pharmazie, 2012, vol. 345, # 7, p. 509 - 516
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9071 - 9088
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 22, p. 5053 - 5059
[4] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 69 - 78
[5] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 529 - 539
