Réaction #1047

Équation de réaction

methanol

compound ( 3 )

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

→

compound ( 4 )

Rendement 66.0%

4-(4-phenoxyphenyl)piperidine

Rendement 66.0%

Solvants

acetic acid

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source