p-Anisoyl chloride → HCID 12940186, compound

Participants

Reaction Steps

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (5 g, 0.019 mole), 200 ml of benzene and 25 ml of 20% NaOH was cooled 10° and a solution of 4-methoxy benzoyl chloride (3.3 g, 0.019 mole) in benzene was added dropwise with stirring. The mixture was stirred in the cold for 30 minutes and at room temperature for 1 hour. The solid was collected after removal of the solvent and chromatographed over silica gel using benzene-methanol (6:1) as eluant. The major fraction (3.8 g) was converted to the HCl salt with hydrogen chloride in 2-propanol. The solvent was removed from the salt in vacuo whereupon the salt was twice recrystallized from methanol-ether, once from 2-propanol and again from absolute ethanol-ethyl acetate to yield 0.8 g of the desired product m.p. (decomposed at 244°-6°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR14##

Provenance & Evidence