Reaction #1047

Reaction equation

methanol

compound ( 3 )

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

→

compound ( 4 )

Yield 66.0%

4-(4-phenoxyphenyl)piperidine

Yield 66.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   OtherAfter 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
   OtherThe organic layer was dried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Otherto obtain a residue which
9. 9
   Otherwas then purified by silica gel column chromatography (methylene chloride:methanol=20:1!)

Procedure

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