Allyl chloride → Hydrochloric Acid

Participants

Reaction Steps

A mixture of 2.19 g of trans-7-methoxy-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine, 0.80 g of allyl chloride, 2.0 g of calcium carbonate in 20 ml of dry dimethylformamide is heated at 80° for 16 hours. After dilution with water the product is extracted with ether. After drying over magnesium sulfate the solvent is removed in vacuo. Acidification with ethanolic hydrochloric acid affords trans-4-allyl-7-methoxy-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride. Hydrogenation of said compound in the presence of 500 mg of 10% palladium on carbon catalyst at 3 atm. pressure for 6 hours at room temperature in water affords trans-7-methoxy-4-propyl-1,2,3,4a,5,10b-hexahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride.

Provenance & Evidence