Application of 954-81-4, A common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
[69] Potassium carbonate (13.57 g, 98.20 mmol), pyrrolidine (4.47 ml, 54.01 mmol) and sodium iodide (7.359 g, 49.098 mmol) were added to ethanol/acetone (1:1) at room temperature and stirred for 1 hour. To the reaction mixture was slowly added N – (5-bromopentyl)phthalimide (2) (10.60 g, 49.10 mmol), and the resulting reaction mixture was refluxed at 50 0C for 24 hours. After the reaction was completed, the resulting white solid was filtered and the solvent was evaporated under reduced pressure. Afterwards, the obtained residue was extracted with a saturated IN NaOH aqueous solution and dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: dichloromethane :methnol: ammonia water = 100:9:1) to give the target compound (3.27 g, 45 %).[70] 1H-NMR (400 MHz, CDCl3) delta 7.81-7.66 (m, 4H, aromatic), 3.66-3.63 (t, 2H, -CH2 -(CH2)4-NC4H8), 2.51-2.49 (t, 4H, -(CH2)S-NC2H4C2H4), 2.45-2.41 (m, 4H, -(CH2)5-NC2 H4C2H4), 1.77-1.74 (m, 2H, -(CH2VCH2-NC4H8), 1.68-1.55 (m, 4H, -CH2-CU2-CU2 – CH2-CH2-NC4H8), 1.36-1.32 (m, 2H, -CH2-CH2-CH2 -CH2-CH2-NC4H8).
The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.