With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.127264-14-6,5-(2-Bromoethyl)-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.
Example 9:Preparation of darifenacin hydrochloride:To 3-(S)-(+)-(l-carbamoyl-l,l-diphenyl methyl) pyrrolidine tartrate (100 grams) taken in water (500 ml), a solution of aqueous sodium hydroxide was added till the pH reached 14. The reaction mixture was stirred for 20 min at 25-300C, sodium chloride(150 grams) was added to it and stirred further for 20min. The reaction mixture was heated to 55-600C and extracted with toluene. The toluene layer was washed with 5percent sodium chloride solution and the solvent distilled off under reduced pressure. The residue was dissolved in acetonitrile, 5-(2-bromoethyl) 2,3-dihydrobenzofuran (66 grams dissolved in 800 ml acetonitrile) and potassium hydroxide (13 grams) was added to it.The reaction mixture was heated to 40-500C and stirred for 18 hrs. The reaction mixture was cooled to 25-30¡ãC and filtered. The acetonitrile solvent was distilled off under reduced pressure. The residue was dissolved in acetone, cooled to 0-5 ¡ãC and hydrochloric acid (36 ml) was added to it. The temperature was raised to 25-30¡ãC and stirred for 12 hrs. The reaction mixture was cooled to 0-5¡ã C, the solid obtained was filtered, washed with acetone and dried. It was purified using methanol and acetone to provide the title compound as a white solid. Yield: 75 grams Example 11:Preparation of darifenacin hydrobromide:To 3 -(S)-(+)-(l -carbamoyl -1,1 diphenyl methyl) pyrrolidine tartrate (100 grams) taken in water (500 ml), a solution of aqueous sodium hydroxide was added till the pH reached 14. The reaction mixture was stirred for 20 min at 25-30¡ãC and sodium chloride(150 grams) was added to it and stirred for 20min. The reaction mixture was heated to55-6O0C and extracted with toluene. The toluene layer was washed with 5percent sodium chloride solution and the solvent distilled off under reduced pressure. The residue was dissolved in acetonitrile, 5-(2-bromoethyl)-2,3-dihydrobenzofuran (66 grams dissolved in 800 ml acetonitrile) and potassium hydroxide (13 grams) was added to it. The reaction mixture was heated to 40-50¡ãC and stirred for 18 hrs. The reaction mixture was cooled to 25-30¡ãC and filtered. The acetonitrile solvent was distilled off under reduced pressure. The residue was dissolved in acetone, cooled to 0-5¡ãC and hydrobromic acid (36 ml) was added to it. The temperature was raised to 25-30¡ãC and stirred for 12 hrs. The reaction mixture was cooled to 0-5¡ã C, the solid obtained was filtered, washed with acetone and dried. It was purified using methanol and acetone to provide the title compound as a white solid.Yield: 75 gramsSOR: +45 (C=I, dichloromethane)
127264-14-6, The synthetic route of 127264-14-6 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; SATYANARAYANA REDDY, Manne; THIRUMALAI RAJAN, Srinivasan; VENKATESH, Mummadi; WO2008/126106; (2008); A2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem
