4-Fluorobenzoyl chloride → HCID 12940220, compound

Participants

Reaction Steps

To a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine, (7 g, 0.026 mole) in 200 ml of toluene and 50 ml of 20% NaOH, was added dropwise 4.5 g of 4-fluorobenzoyl chloride. The mixture was stirred in the cold for 1 hour and at room temperature for 1 hour. The resulting solid product was collected and chromatographed over silica gel using ethyl acetate-methanol-chloroform (3:1:1) as eluant. The major fraction (5.0 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and ether, isolated by removal of the solvent and recrystallized from methanol-ether to yield 2.3 g of the desired product, m.p. (decomposed at 257°-8°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR29##

Provenance & Evidence