Allyl bromide → HCID 13109061, compound

Participants

Reaction Conditions

Reaction Steps

27.7 g. (84 mmol) (-)-7-Hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in 430 ml. ethanol are mixed with 9.18 g. (75.9 mmol) allyl bromide and 17.6 g. (209 mmol) sodium bicarbonate. The reaction mixture is heated for 3 hours at 80° C., while stirring. After cooling and evaporating in a vacuum, the residue is partitioned between water and methylene chloride. The usual working up and chromatographic purification (silica gel; chloroform) gives 22.0 g. of a pale yellow foam. By crystallisation from isopropanol-diethyl ether, there is obtained (+)-2-allyl-7-hydroxy-6-methoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline in the form of colourless crystals; m.p. 108°-112° C.

Provenance & Evidence