Reference of 954-81-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 954-81-4, name is N-(5-Bromopentyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.
General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained. 2-(5-(Pyrrolidin-1-yl)pentyl)isoindoline-1,3-dione (1) [55]. Procedure M1. Reaction of 2-(5-bromopentyl)isoindoline-1,3-dione [37] (0.5 g, 1.69 mmol) with pyrrolidine (0.13 g, 1.86 mmol) and K2CO3 (0.7 g,5.1 mmol) in acetonitrile (25 mL), after 20 h, column chromatography gave oil product. Yield 0.35 g(73%). TLC (S3) Rf = 0.13. MW 286.17. Formula: C17H22N2O2. MS: m/z 287.28 [M + H]+. 1H-NMR(300 MHz, CDCl3) delta ppm: 7.89-7.77 (m, 2H), 7.78-7.65 (m, 2H), 3.69 (t, J = 6.9 Hz, 2H), 3.00 (m, 4H),2.06-1.88 (m, 4H), 1.81-1.65 (m, 4H), 1.48-1.21 (m, 4H). Hydrochloride salt: M.p. 190C. Elementalanalyses (%) for C17H22N2O2 HCl Calc. C 63.25; N 8.63; H 7.18, found: C 62.73; N 8.54; H 7.27.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-(5-Bromopentyl)phthalimide, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem