Ammonia → HCID 19874551, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl] phenoxymethyl]-5-benzyloxy-4H-pyran-4-one (2 g) in methanol (10 ml) was treated with ammonia solution, SG 0.88, (5 ml) and heated to 120° C. in a sealed vessel for 18 hours. After evaporation of the solvent in vacuo the residue was crystallised from ethanol to give 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]-propyl]phenoxymethyl]-5-benzyloxy-1H-pyrid-4-one (1.6 g , which was dissolved in methanol and the solution acidified with 2M hydrochloric acid solution to pH 1.5-2.0 and hydrogenated at room temperature and pressure over 10% palladium on charcoal. After filtration and evaporation of the solvent in vacuo the residue was treated with 1.2M sodium hydrogen carbonate solution (5 ml) and extracted with ethyl acetate (3×50 ml), dried (magnesium sulphate), filtered and evaporated under reduced pressure to give an oil. This was dissolved in methanol and treated with methanolic hydrogen chloride. Evaporation in vacuo gave 2-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyl]phenoxymethyl]-5-hydroxy-1H-pyrid-4-one dihydrochloride as a (37:63) mixture of diastereoisomers.

Provenance & Evidence