Methanol → 6-[4-(4-Benzyloxyphenyl)piperidin-3-yloxymethyl]-4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazine

Temperature

100 °C

0.090 g of benzyl 4-(4-benzyloxyphenyl)-3-[4-(3-methoxypropyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate is dissolved in 3 ml of dioxane. 3 ml each of methanol and 40% KOH are added and the reaction mixture is stirred in a sealed flask at 100° C. over 3.5 hours. The reaction mixture is subsequently cooled to room temperature, diluted with 10 ml of water and extracted with tert-butyl methyl ether (3×30 ml). The combined organic phases are washed with 10 ml of water, then 10 ml of brine, dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F).

1. temperatureThe reaction mixture is subsequently cooled to room temperature
2. extractionextracted with tert-butyl methyl ether (3×30 ml)
3. washThe combined organic phases are washed with 10 ml of water
4. dry with material10 ml of brine, dried over sodium sulphate
5. filtrationfiltered
6. concentrationconcentrated by evaporation

ORD record

ord-ad073a5d378c4edfbf08c7e8c109113c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842688B2