Acetic Acid → HCID 67561572, compound

HRID 1683122Notes

Reaction equation

HRID 1683122 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([C:14]([NH2:16]=O)=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C.[H][H].[ClH:31]>C(OCC)(=O)C.[Pd]>[ClH:31].[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:11]2([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 88283475[1-Benzyl-4-(4-fluorophenyl)piperidine-4-carbonyl]-oxidoazaniumHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67561572HCID 67561572, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-4-(4-fluoro-phenyl)-piperidine-4-carboxylic acid amide N-oxide (5.3 g, 16.3 mmol) and 10% palladium-on-carbon (0.6 g) and acetic acid (100 mL) were combined in a pressure vessel. The reaction mixture was treated with hydrogen on a Parr apparatus at an initial pressure of 53 psi of hydrogen. When hydrogen consumption stopped the catalyst was removed by filtration. The filtrate was evaporated in vacuo to give a residue. The residue was dissolved in ethyl acetate (150 mL), acidified by the addition of 12M aqueous hydrochloric acid solution (5 mL), and heated to reflux for 10 minutes. The mixture was cooled to ambient temperature to give a solid which was collected by filtration, rinsed with ethyl acetate, recrystallized from methanol/ethyl acetate to give the title compound.

Workup

  1. customWhen hydrogen consumption
  2. customwas removed by filtration
  3. customThe filtrate was evaporated in vacuo
  4. customto give a residue
  5. temperatureheated
  6. temperatureto reflux for 10 minutes
  7. customto give a solid which
  8. filtrationwas collected by filtration
  9. washrinsed with ethyl acetate
  10. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-b8e0120a74164cc3bbe7a88a93974078
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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