Methanol → 4-(4-Phenoxyphenyl)piperidine

HRID 992363

Reaction equation

HRID 992363 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].[Pd].C(O)(=O)C>[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

5

Reactant 2

HCID 887MethanolHCID 225999894-(4-Phenoxyphenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 110759844-(4-Phenoxyphenyl)piperidineYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To a 100 ml methanol solution of 3.51 g of the compound (8) synthesized in Example 1 were added 200 mg of palladium carbon and 1 ml of acetic acid for hydrogenation at atmospheric pressure and room temperature. After the completion of the reaction, the insolubles were filtered off, then the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in methylene chloride and adjusted by a 10% aqueous solution of sodium hydroxide to a pH 9 to 10, then was shaken. The organic layer was dried, filtered, then condensed 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-referenced compound (9) in an amount of 2.32 g (yield 66%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe insolubles were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in methylene chloride
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customcondensed under reduced pressure
  8. customto obtain a residue which
  9. customwas then purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-68b176c97cf44b6fa785f4d2168d0504
Source dataset
uspto-grants-2002_10
Patent number
US06469010B1

Linked notes

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