4-Chlorobenzoyl chloride → HCID 12940208, compound

Participants

Reaction Steps

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (8 g, 0.03 mole), 200 ml of toluene and 80 ml of 20% NaOH was cooled to 10° in an ice bath at which point 4-chlorobenzoyl chloride (5.5 g, 0.03 mole) was added dropwise with stirring. The mixture was stirred in the cold for 1 hour whereupon the solid was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol-chloroform (3:1:1) as eluant. The major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in 2-propanol-ethyl acetate and was recrystallized from methanol-ethyl acetate twice to yield 4.2 g of the desired product, m.p. (decomposed at 253°-4°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR23##

Provenance & Evidence