Ethanol → Lofexidine

Participants

Reaction Steps

58.6 (0.3089 mols) of titanium tetrachloride are dissolved in a mixture of 700 ml of absolute chloroform and 25 ml of tetrahydrofuran at 0° C. and are mixed with 35.0 g (0.1263 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide. A solution of 74.0 g (0.6056 mols) of 4-dimethylaminopyridine is then added dropwise very slowly at 0° C. with stirring and the mixture is further stirred for 36 hours at room temperature after the solution has been added. After working up and after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 21.0 g of (-)-2-[1-(2,6-dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1], are obtained, Mp.: 126°-127° C.: [α]D20 =-80.2° (c=1/ethanol).

Provenance & Evidence