HCID 131712268, compound → HCID 54332767, compound

Participants

Reaction Steps

In a 150 ml glass hydrogenation vessel were placed 1 g (2.45 mole) of the 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-5H-dibenz[b,f]azepine-11-one prepared in Example 6 dissolved in 35 ml of glacial acetic acid and 1 g of 10% palladium on carbon. The vessel was placed on a Parr-pressure apparatus, flushed with nitrogen, evacuated, pressurized to 60 psi hydrogen and shaken for 4 days with daily pressure adjustment. The vessel was then flushed with nitrogen, evacuated, filtered through a Celite pad, washed with absolute methanol and concentrated on a rotary evaporator under reduced pressure. The residue was dissolved in chloroform and extracted with 10% NaHCO3 to remove excess acid. The organic phase was dried with magnesium sulfate, filtered and concentrated. The reaction was repeated on another 1 g lot of 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-5H-dibenz[b,f]azepine-11-one prepared in Example 6. The products were combined yielding 1.6 g crude material. The 1.6 g was applied to chromatographic plates (20-20 cm 2.5 mm prep tlc plates silica gel PF-254) and eluted with diethyl ether saturated with ammonia gas. The plates were air dried and developed four times until separation was maximized by UV inspection. The two bands were isolated, extracted with methanol, concentrated, redissolved in chloroform, filtered and concentrated on a rotary evaporator yielding 0.600 g of 10-carboethoxypropyl-5-(3'-dimethylaminopropyl)-10,11-dihydro-5H-dibenz[b,f]azepine and 0.805 g of starting material. The product (0.600 g) containing trace amounts of starting material was rechromatographed (using silica gel PF-254 20×20 cm 2.5 mm prep plates) and eluted with methanol:chloroform 1:9. The isolation procedure was the same as above.

Provenance & Evidence