Chloride → HCID 14719524, compound

Participants

Reaction Steps

10.0 g of 3-t-butyloxycarbonyl-6-chloro-7, 8-dihydroxy-1-(4'-hydroxyphenyl) 2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in 100 ml of DMF. To this was added 1.25 g of a 50% sodium hydride mineral oil dispersion under an argon atmosphere. The reaction was stirred at ambient temperature for 15 minutes and 3.59 g of 4-methozybenyl chloride was added. The reaction was stirred for 16 hours at ambient temperature then poured into a large volume of water. The mixture was then extracted with ethyl acetate. The extracts were washed with water dried over magnesium sulfate and concentrated to yield an oil. The crude product was dissolved in 100 ml. of acetonitrile and the solution washed with several portions of petroleum ether. The acetonitrile solution was concentrated and seeded with crystals of the product. The solution was allowed to stand in a freezer overnight with a resultant of white solid. Additional solid was obtained after concentration of the mother liquor. The solid (5.57 g) was heated for 10 minutes in 100 ml of dichloromethane on a steam bath. The suspension was filtered and the solid washed with warm dichloromethane to yield 3-t-butyloxycarbonyl-6-chloro-8-hydroxy-7-(4-methoxybenzyloxy)-1-(4 -hydroxyphenyl)-2,3,4,5 tetrahydro-1-H-3-benzazepine, M.P. 190°-192° C.

Provenance & Evidence