Benzoyl chloride, 3,4,5-trimethoxy- → HCID 12940202, compound

Participants

Reaction Steps

A solution of 3,4,5-trimethoxy benzoyl chloride (13 g) in pyridine was added dropwise to 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (13 g) in 200 ml of pyridine, and the solution was warmed at 60°-70° for 30 minutes and poured into ice water. The mixture was extracted with chloroform and the extracts dried over MgSO4, concentrated in vacuo and the concentrated material chromatographed over silica gel using ethyl acetate-methanol-chloroform (4:1:0.5) as eluant. The major fraction (9.9 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol, methanol and ethyl acetate, isolated as a solid and recrystallized from methanol-ethyl acetate and again from methanol to yield 3.6 g of the desired product, m.p. (decomposed at 259°-61°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR20##

Provenance & Evidence