反应详情

A solution of n-butyl lithium (25 mL of 2.1M reagent in hexane, 0.0525 mole) is added dropwise in an N2 atmosphere to a solution of di-isopropylamine (5.6 g) in tetrahydrofuran (100 mL) which is maintained at -20°. This cold solution is then added dropwise to a solution of 4-(1-imidazolylmethyl)benzonitrile (9.15 g) in tetrahydrofuran (250 mL) which is maintained at -50° during addition and for 30 minutes subsequently. The reaction mixture is then cooled to -70° for 30 minutes and then without external cooling for 10 hours. The reaction is quenched by addition of water (300 mL) and extracted with diethyl ether (3×100 mL). The combined ether extracts are extracted with 3N hydrochloric acid (3×60 mL) and the acid extracts are made basic (pH 9) with 6N sodium hydroxide. The crude product is extracted into ether (3×60 mL), and after drying (MgSO4) and solvent evaporation, 4-[1-(1-imidazolyl)ethyl]benzonitrile is obtained. The crude material is dissolved in acetone and treated with ethereal HCl to afford the hydrochloride salt, m.p. 184°-186°.

1. temperatureis maintained at -20°
2. temperatureis maintained at -50° during addition and for 30 minutes subsequently
3. temperatureThe reaction mixture is then cooled to -70° for 30 minutes
4. temperaturewithout external cooling for 10 hours
5. customThe reaction is quenched by addition of water (300 mL)
6. extractionextracted with diethyl ether (3×100 mL)
7. extractionThe combined ether extracts are extracted with 3N hydrochloric acid (3×60 mL)
8. extractionThe crude product is extracted into ether (3×60 mL)
9. customafter drying
10. custom(MgSO4) and solvent evaporation