Lorazepam → 1-(2-Cyanoethyl)-7-chloro-3-hydroxy-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one

Participants

Reaction Steps

1 g of Teba and 8 drops of a 40% methanolic solution of Triton B were added to a suspension of 10 g of 7-chloro-3-hydroxy-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one ("Lorazepam") in 50 ml of acrylonitrile and the mixture was stirred for 24 hours at room temperature. Then the reaction mixture was cooled to 4° C., the precipitate was filtered and recrystallized from ethyl acetate. 1-(2-Cyanoethyl)-7-chloro-3-hydroxy-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one, m.p. 198° to 202° C., was obtained. Without addition of Teba also the disubstituted 1-(2-cyanoethyl)-7-chloro-3-(2-cyanoethoxy)-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine-2-one, m.p. 210° to 213° C. (from acetonitrile), is obtained.

Provenance & Evidence