Acetic Acid → 4-(4-Phenoxyphenyl)piperidine

HRID 1060987Notes

Reaction equation

HRID 1060987 reaction equation
CO.[O:3]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=O)C.[OH-].[Na+]>C(Cl)Cl.[C].[Pd]>[O:3]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 225999894-(4-Phenoxyphenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 110759844-(4-Phenoxyphenyl)piperidineYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

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 a residue, 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%).

Workup

  1. customwas hydrogenated under atmospheric pressure at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe insolubles were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue obtained
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a residue, which
  10. customwas then purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-bdb3b3093ca14593906a193f6a7401b9
Source dataset
uspto-grants-2003_02
Patent number
US06525199B1

Reaction notes

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