4-Methylbenzoyl Chloride → HCID 12940204, 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 (9 g, 0.034 mole) in 300 ml of toluene and 75 ml of 20% NaOH was added dropwise p-toluoyl chloride (6 g, 0.035 mole). The mixture was stirred in the cold for 1 hour and allowed to come to room temperature. The solid was collected by filtration and the toluene layer concentrated in vacuo whereupon the solid and concentrate were combined and chromatographed over silica gel using ethyl acetate-methanol (4:1) as eluant. The major fraction (6.2 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate, isolated and twice recrystallized from methanol-ethyl acetate to yield 3.2 g of the desired product, m.p. (decomposed at 268°-70°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR21##

Provenance & Evidence