Related Products of 5332-06-9, These common heterocyclic compound, 5332-06-9, name is 4-Bromobutanenitrile, 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.
(trans) 1-(1 H-benzimidazol-2-ylmethyl)-2,3,3a,4,5,9b-hexahydro-1 H-pyrrolo[3,2- /?]quinoline (0.032 g, 0.11 mmol), potassium carbonate (0.075 g, 0.55 mmol), 4- bromobutanenitrile (0.024 g, 0.16 mmol), and potassium iodide (5 mg) in 3 ml_ of N,N-dimethyIformamide were heated to 80 2C in a sealed tube for 16 hours. The mixture was allowed to cool to room temperature and quenched with 5 ml_ of water. The mixture was extracted 3 times with 5 mL of dichloromethane and the combined organic layers concentrated. The residue was dissolved in 20 mL of a 2M ammonia solution in methanol and hydrogenated under 40 psi of hydrogen for 18 hours, with 30 mg of raney nickel as catalyst. The catalyst was filtered off over celite and the filtrate concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of aqueous ammonia in acetonitrile to yield 29 mg (70%) of (trans) 4-[2-(2,3,3a,4,5,9b-hexahydro-1 H-pyrrolo[3,2-/7]quinolin-1 -ylmethyl)-1 H- benzimidazol-1-yl]-1 -butanamine. 1 H NMR (400 MHz, METHANOL-D4) delta ppm 1.1 (m, 2 H), 1.4 (m, 2 H), 1.7 (m, 2 H), 1.8 (m, 1 H), 2.1 (m, 1 H), 2.4 (m, 1 H), 2.5 (t, J=7.4 Hz, 2 H), 2.7 (m, 1 H), 2.8 (m, 2 H), 2.9 (m, 1 H), 3.6 (d, J=8.6 Hz, 1 H), 3.6 (d, J=13.6 Hz, 1 H), 3.7 (m, 1 H), 3.8 (m, 1 H), 4.7 (d, J=13.6 Hz, 1 H), 7.2 (m, 2 H), 7.4 (m, 2 H), 7.6 (m, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (d, J=6.4 Hz, 1 H); MS m/z376(M+1).
The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts