New learning discoveries about

Synthetic Route of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

(cis) 1-(1 /-/-Benzimidazol-2-ylmethyl)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10- phenanthroline (0.045 g, 0.14 mmol), 2-(5-bromopentyl)-1 /-/-isoindole-1 ,3(2H)-dione (0.062 g, 0.21 mmol), potassium iodide (5 mg), and N,N-diisopropylethylamine (0.050 g, 0.31 mmol) in 3 mL of dimethylformamide were heated to 80 9C for 16 hours. The mixture was allowed to cool to room temperature and hydrazine (0.4 mL, 14.0 mmol) was added. The mixture stirred at room temperature overnight. The mixture was quenched with water and extracted 3 times with ethyl ether. The ether layers were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of 30% aqueous ammonium hydroxide in acetonitrile to yield 0.01O g (18%) of (cis)-5-[2-(3,4,4a,5,6,10b- hexahydro-1 ,10-phenanthrolin-1 (2/-/)-ylmethyl)-1 H-benzimidazol-1-yl]-1- pentanamine. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.0 (m, 2 H), 1.3 (m, 3 EPO H), 1.4 (s, 2 H), 1.6 (m, 1 H), 1.7 (m, 2 H)1 2.1 (m, 1 H), 2.3 (m, 2 H), 2.5 (m, 3 H), 2.8 (m, 1 H), 2.9 (m, 1 H), 3.1 (m, 1 H), 3.4 (s, 1 H), 3.5 (d, J=13.9 Hz, 1 H), 3.9 (m, 1 H), 4.1 (m, 1 H), 4.2 (d, J=13.9 Hz, 1 H), 7.2 (m, 2 H), 7.3 (m, 2 H), 7.5 (d, J=7.1 Hz, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (s, 1 H); MS m/z404 (M+1).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
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