Uses
N-(3-Bromopropyl)phthalimide is used in synthesis of several organic compounds including that of flavonoid derivatives which act as selective ABCC1 modulators with potential use as pharmacological tools for investigation of the role of ABCC1. It is also used in the synthesis of Hederagenin which is a triterpene template for the development of new antitumor compounds.
Synthesis
In 50 mL of DMF, 0.025 mol of phthalimide potassium salt, 0.10 mol of 1,3-dibromopropane and 0.5 g of TBAB were added and the reaction was carried out at 70°C for 2.0 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The organic phase was sequentially washed with water, dried, concentrated and allowed to stand overnight to give 5.91 g of N-(3-bromopropyl)phthalimide as a white solid with a melting point of 70-73°C and a yield of 88.3%.
Purification Methods
Place it in a Soxhlet and extract it with Et2O, whereby the bis-phthalimido impurity is not extracted. Evaporate the Et2O and recrystallise the residue from EtOH, aqueous EtOH or pet ether. [Gabriel & Weiner Chem Ber 21 2669 1888, Gaudry Can J Chem 31 1060 1953, Beilstein 21/10 V 1277.]
References
[1] Patent: CN107382980, 2017, A. Location in patent: Paragraph 0035; 0036; 0037; 0038
[2] Patent: CN107540647, 2018, A. Location in patent: Paragraph 0049-0051
[3] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 69 - 78
[4] Chemistry - A European Journal, 2014, vol. 20, # 6, p. 1530 - 1538
[5] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 7, p. 1223 - 1227
