Methanol → 4-(4-Phenoxyphenyl)piperidine

HRID 951

Reaction equation

HRID 951 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 (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%).

Workup

  1. customAfter the end 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. concentrationconcentrated 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-33d9f641c6034e9a99040843b1b7b174
Source dataset
uspto-grants-1998_03
Patent number
US05723475

Linked notes

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