Reaktion #1047

Reaktionsgleichung

methanol

compound ( 3 )

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

→

compound ( 4 )

Ausbeute 66.0%

4-(4-phenoxyphenyl)piperidine

Ausbeute 66.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the end of the reaction
2. 2
   Filtrationthe insolubles were filtered off
3. 3
   Einengenthe filtrate was concentrated under reduced pressure
4. 4
   workup.DISSOLUTIONThe obtained residue was dissolved in methylene chloride
5. 5
   SonstigeThe organic layer was dried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   Sonstigeto obtain a residue which
9. 9
   Sonstigewas then purified by silica gel column chromatography (methylene chloride:methanol=20:1!)

Vorschrift

To a 100 ml methanol solution of 3.51 g of the compound (3) synthesized in Reference Example 3 were added 200 mg of palladium carbon and 1 ml of acetic acid for hydrogenation at atmospheric pressure and room temperature. After the end of the reaction, the insolubles were filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in methylene chloride, then adjusted by a 10% aqueous solution of sodium hydroxide to pH=9 to 10, then was shaken. The organic layer was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=20:1!) to obtain the above-reference compound (4) in all amount of 2.32 g (yield of 66%).

Quelle