5394-18-3

white crystalline powder

N-(4-Bromobutyl)phthalimide is used in organic synthesis and the production of pharmaceutical. It can react with 1-phenyl-piperazine to get N-[4-(4-phenyl-piperazin-1-yl)-butyl]-phthalimide. It is a useful synthesis reagent used to synthesize B-cyclodextrin derivatives.

reagent type: cross-linking reagent
reagent type: linker

General procedure for the synthesis of N-(4-bromobutyl)phthalimide from 1,4-dibromobutane and 3-hydroxy-1H-isoindol-1-one: phthalimide (148 mg, 1 mmol), 1,4-dibromobutane (1.080 g, 5 mmol) and potassium carbonate (276 mg, 2 mmol) were added to acetone (3 mL) and the reaction mixture was refluxed for 2 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was purified by column chromatography using petroleum ether: acetone (40:1) as eluent to afford N-(4-bromobutyl)phthalimide (260 mg, 92% yield) as a white solid.

[1] Journal of Organic Chemistry, 2004, vol. 69, # 18, p. 6094 - 6099
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 6, p. 1532 - 1536
[3] Angew. Chem., 2018, vol. 130, # 6, p. 1548 - 1552,5
[4] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 74 - 85
[5] Journal of the Chinese Chemical Society, 2013, vol. 60, # 12, p. 1431 - 1436