The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.
501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 2-(3-Fluorophenyl)acetonitrile
2-Chloro-N-(2-chloroethyl)ethanaminium chloride (12.5 g, 70.2 mmol) was stirred in 351 mL of THF. To this mixture was added triethylamine (10.3 mL, 73.7 mmol) and then di-tert-butyl dicarbonate (16.1 g, 73.7 mmol), which was stirred for 19 hours. The reaction was diluted with dichloromethane (250 mL), washed with water (3 x 250 mL), and partitioned between water and dichlormethane. The organic layer was dried over sodium sulfate, filtered, and concentrated to afford tert-butyl bis(2-chloroethyl)carbamate. A mixture of 3-fluorophenylacetonitrile (200 mg, 1.48 mmol) and tert-butyl bis(2- chloroethyl)carbamate (358 mg, 1.48 mmol) was dissolved in 14.8 mL of anhydrous DMSO. The reaction was purged with a stream of nitrogen and cooled to 18 0C. To this reaction was added sodium hydride (358 mg, 1.48 mmol), which was then warmed to ambient temperature and stirred for 2 hours. The reaction was warmed to 50 0C and stirred for 17 hours. The mixture was diluted with dichloromethane (40 mL), washed with water (3 x 40 mL), and partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate, filtered, concentrated, and subjected to silica gel chromatography eluting with 0-20% EtOAc in hexanes. Collection of product containing fractions and removal of solvent yielded tert-butyl 4-cyano-4- (3-fluorophenyl)piperidine- 1 -carboxylate. The title compound was prepared in a manner analogous to that described inExample 1 that gave a proton NMR spectrum consistent with theory and a high resolution mass spectrum (ES+) m/z of 406.1575 calculated for M+H+ [C23H20FiN3O3: 406.1562]: 1H NMR (500 MHz, CD3OD) delta 9.56 (d, J= 7.1 Hz, IH), 8.70 (s, IH), 8.47 (d, J= 9.0 Hz, IH), 8.18 (t, J= 7.9 Hz, IH), 7.72 (t, J= 6.8 Hz, IH), 7.46-7.51 (m, IH), 7.37 (d, J= 8.6 Hz, IH), 7.30 (d, J= 10.0 Hz, IH), 7.16 (t, J= 8.4 Hz, IH), 4.67 (bs, 2H), 3.65 (m, 2H), 3.37 (m, 2H), 2.46 (d, J= 14.2 Hz, 2H), 2.29 (m, 2H).
The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK & CO., INC.; WO2009/51715; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts