Hydrogen Bromide → 1-(5-Methoxy-2-methylphenyl)piperazine

Temperatur

90 °C

To 505 mg (2.0 mmol) of 3-[2-(5-Methoxy-2-methyl-phenylamino)-ethyl]-oxazolidin-2-one in a flask was added 2 mL of 48% HBr in acetic acid, 1 mL of acetic acid, and 1 mL of anisole, and the mixture was heated at 90° C. for six hours. The solution was allowed to cool to room tempterature, and 5 mL of CH2Cl2 was added. The product crystallized and was isolated by filtration. The solids were dissolved in 55 mL of ethanol, 201 mg (2 mmol) of triethylamine were added, and the solution was heated at reflux for 3 hours. The solution was then concentrated in vacuo to give a residue that was partitioned between ether and water. The phases were separated, and the aqueous phase as basified with 1M NaOH. The aqueous phase was then extracted twice with ethyl acetate. The combined ethyl acetate phases were washed once with brine, dried over Na2SO4, filtered, and acidified with 2M HCl in ether. The product was isolated via filtration.

1. additionwas added
2. customThe product crystallized
3. customwas isolated by filtration
4. temperaturethe solution was heated
5. temperatureat reflux for 3 hours
6. concentrationThe solution was then concentrated in vacuo
7. customto give a residue that
8. customwas partitioned between ether and water
9. customThe phases were separated
10. extractionThe aqueous phase was then extracted twice with ethyl acetate
11. washThe combined ethyl acetate phases were washed once with brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. customThe product was isolated via filtration

ORD-Eintrag

ord-fdf0f330a9014bc58c3fb11929d058ff

Quelldatensatz

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07157464B2