Reaktion #2075759

Reaktionsgleichung

methanol

4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine

acetic acid

sodium hydroxide

→

4-(4-phenoxyphenyl)piperidine

Ausbeute 66.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas hydrogenated under atmospheric pressure at room temperature
2. 2
   SonstigeAfter completion of the reaction
3. 3
   Filtrationthe insolubles were filtered off
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigeThe residue obtained
6. 6
   SonstigeThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Sonstigeto give aresidue, which
10. 10
    Sonstigewas then purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Vorschrift

To an 100 ml methanol solution of 3.51 g of the 4-(4-phenoxyphenyl)-1,2,3,6-tetrahydropyridine synthesized in Step B was added a 200 mg of palladium carbon and 1 ml of acetic acid. The resultant mixture was hydrogenated under atmospheric pressure at room temperature. After completion of the reaction, the insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was dissolved in methylene chloride, adjusted by 10% aqueous sodium hydroxide solution to pH=9 to 10, then shaken. The organic layer was dried, filtered, then concentrated under reduced pressure to give aresidue, which was then purified by silica gel column chromatography (methylene chloride:methanol=20:1) to give the above-referenced compound, 4-(4-phenoxyphenyl)piperidine in an amount of 2.32 g (yield 66%).

Quelle