Dimethylamine → HCID 131719461, compound

Participants

Reaction Steps

A mixture of 9-bromo-1,2-dihydro-7-(2-propynyl)-benzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one (4.0 gm, 11.3 mmoles), paraformaldehyde (3 gm), dimethylamine (40% in water, 4 gm, 3 eq) and CuCl (150 mg) in 1,4-dioxane (50 ml) was stirred at room temperature for 30 minutes, then heated on a water bath (50° C.) for 2 hours. When the reaction was over, the mixture was diluted with dichloromethane (200 ml). The insolubles were filtered through a pad of celite. The solution was concentrated to a crude oil (7.5 gm). The desired product was purified by flash chromatography on a silica gel column (SiO2, 65 gm, eluted with 1% CH3OH:0.5% diethylamine:99% DCM, 1.2 l). The material thus obtained weighed 4.58 gm (98%). This oily product was dissolved in ether and added to a solution of fumaric acid (1.27 gm, 1.0 eq) in hot ethanol (15 ml). Crystals (4.75 gm) were formed slowly over a 2 hour period. Recrystallization from hot acetone (350 ml, concentrated down to 75 ml) yielded 4.21 gm, 71%, of light yellow crystals, top: 177°-179° C.

Provenance & Evidence