Methanol → HCID 15225467, compound

Participants

Reaction Steps

1.9 g of 2,3-dihydro-5-(4-methoxyphenyl)-6-methyl-2-[2-(4-(4-methylpyridin-2-yl)piperazin-1-yl)ethyl]pyrrolo[1,2,3-de]-1,4-benzoxazine (Preparation see Example 1) were dissolved in 5 ml of anhydrous dichloromethane under a nitrogen atmosphere. The solution was cooled to 0° to 5° C. and 1.5 g of boron tribromide were then added all at once. The reaction mixture was subsequently stirred for 3 hours at room temperature. The reaction mixture was then again cooled to 0° to 5° C. and 10 ml of methanol were added, and the reaction mixture was again stirred for half an hour at room temperature and then evaporated. The residue was dissolved in 20 ml of aqueous ammonia solution (pH=8/9) and the solution was extracted with dichloromethane. The extracts were dried, filtered and concentrated. The crude title compound remaining as a residue was purified by column chromatography using toluene/ethanol 95:5 and crystallized from isopropanol. 1.5 g of 2,3-dihydro-5-(4-hydroxyphenyl)-6-methyl-2-[2-(4-(4-methylpyridin-2-yl)piperazin-1-yl)ethyl]pyrrolo[1,2,3-de]-1,4-benzoxazine were obtained as a white powder having a melting point of 213° to 214° C.

Provenance & Evidence