11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one → HCID 19846062, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 33.4 g (0.122 mol) of 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 28.0 g (0.131 mol) of 2-[2-[(diethylamino)methyl]piperidin-1-yl]ethanamine and 730 ml of anhydrous acetonitrile was stirred for 3 hours at a reaction temperature of 45° C. After standing for 1 hour in an ice bath, the precipitate formed was suction filtered and washed with ice cold acetonitrile. It was dissolved in 400 ml of hot ethanol, 4.6 g of activated charcoal were added, the mixture was filtered whilst hot and the filtrate was evaporated down in vacuo. The residue remaining was dissolved in 150 ml of hot propan-2-ol and stirred at a temperature of 75° C. for 2 hours after the careful addition of 800 ml of ethyl acetate. The mixture was then left to stand for 2 hours at ice bath temperature, the crystals produced were suction filtered and thoroughly washed three times with 20 ml aliquots of ethyl acetate. 37.0 g (62% of theory) of colourless crystals were obtained, m.p. 200°-202° C.

Provenance & Evidence