Diethylaminoethyl chloride → 11-(2-Diethylamino-ethyl)-6,11-dihydro-2,6-dimethyl-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one

Participants

Reaction Steps

A mixture consisting of 7.2 gm of 6,11-dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 70 ml of dimethyl formamide and 1.9 gm of 50% sodium hydride in mineral oil was stirred at 30° to 50° C. in a nitrogen atmosphere for 30 minutes. Thereafter, a solution of 6.8 gm of 2-diethylaminoethyl chloride in 30 ml of dimethyl formamide was added dropwise, and the mixture was stirred at 100° C. for 2 hours and then evaporated in vacuo. The residue was admixed with an aqueous potassium carbonate solution, and the mixture was extracted with ether. The evaporation residue of the combined ether extracts, which were dried with sodium sulfate, was purified in a silica gel column and recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 62% of theory of the compound of the formula ##STR13## which had a melting point of 91°-93° C.

Provenance & Evidence