Diethyl Ether → 11-(2'-dimethylamino-ethyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Participants

Reaction Steps

9.0 gm of 6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one were dissolved in 200 ml of hot absolute xylene, 2.1 gm of 50% sodium hydride in mineral oil were added to the solution, and the mixture was refluxed for 2 hours. Then, 5.3 gm of 2-dimethylamino-ethyl chloride were added dropwise, and the mixture was refluxed for 16 hours more. The cooled reaction mixture was shaken with a mixture of ether and water, and the organic phase was separated and extracted with dilute acetic acid. Then the acidic aqueous layer was made alkaline with concentrated ammonia, and the precipitated oil was extracted with ether. After evaporation of the ether extract, the residue was distilled, yielding 7.0 gm (59% of theory) of 11-(2'-dimethylamino-ethyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, b.p. 163°-164° C. at 0.01 mm Hg.

Provenance & Evidence