Epichlorohydrin → HCID 19788278, compound

Participants

Reaction Steps

A mixture of 3-hydroxy-2-methyl-4-oxopyrane (12.6 g), sodium hydroxide (4 g), epichlorohydrin (9.25 g) and water (50 ml) is stirred at room temperature, under nitrogen atmosphere, for 3 hours; then it is extracted four times with chloroform (120 ml) and the organic extracts are combined, washed with water, dried and evaporated to dryness yielding 8.3 g of 3-(2,3-epoxypropoxy)-2-methyl-4-oxopyrane. A mixture of said product and 2-aminotetralin (7.3 g) in absolute ethanol (100 ml) is charged into a sealed vessel, heated to 80° C. for 5 hours, then cooled and evaporated under reduced pressure. The obtained residue is dissolved into ethyl acetate and a solution of fumaric acid in ethyl acetate is then added thereto. The precipitate which forms is recovered by filtration and crystallized from ethanol affording N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-methyl-4-oxopyran-3-yloxy)propanamine hydrogenfumarate ((i): R=H, Ar=radical 10 wherein Z is methyl, and the chain is attached to position 2 of the tetralin moiety).

Provenance & Evidence