Potassium Carbonate → 2-Bromo-4-(4-hydroxy-piperidin-1-yl)-benzoic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[Br:11].[OH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:17]2[CH2:18][CH2:19][CH:14]([OH:13])[CH2:15][CH2:16]2)=[CH:6][C:5]=1[Br:11]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
A mixture of 2-bromo-4-fluoro-benzoic acid methyl ester (2.06 g, 8.84 mmol), 4-hydroxy piperidine (1.86 g, 18.4 mmol), and potassium carbonate (1.33 g, 9.62 mmol) in acetonitrile (25 mL) is heated to 90° C. for 17 h. The mixture is concentrated and partitioned between ethyl acetate and water. The solvent layers are separated and the aqueous layer is extracted with ethyl acetate (3×). The combined ethyl acetate layers are dried (MgSO4), filtered, and concentrated under reduced pressure. The residue is purified on silica (120 g) using a gradient of 0% to 90% ethyl acetate in heptane to provide the title compound (2.10 g, 76%) LC-ES/MS m/z 314.0 (M+1)
Aufarbeitung
- concentrationThe mixture is concentrated
- custompartitioned between ethyl acetate and water
- customThe solvent layers are separated
- extractionthe aqueous layer is extracted with ethyl acetate (3×)
- dry with materialThe combined ethyl acetate layers are dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue is purified on silica (120 g)
Quellen und Nachweise
- ORD-Eintrag
- ord-dc285c180cbf41a494266555d2ec4191
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08153624B2
Notizen zur Reaktion
Wird geladen…