Acetic Acid → 4-Phenylpiperidine-4-carboxamide monohydrochloride

HRID 343500Notes

Reaction equation

HRID 343500 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[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.[ClH:28]>C(OCC)(=O)C.[Pd]>[ClH:28].[C:18]1([C:11]2([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 88146759(1-Benzyl-4-phenylpiperidine-4-carbonyl)-oxidoazanium

Product 1

HCID 30171294-Phenylpiperidine-4-carboxamide monohydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Combine 1-benzyl-4-phenylpiperidine-4-carboxylic acid amide N-oxide (529 g, 1700 mmol), 10% palladium-on-carbon (25 g), and acetic acid (5 L) in an autoclave. Flush the autoclave with nitrogen and then charge with 255 psi of hydrogen. Stir while recharging the autoclave with hydrogen as required to maintain the pressure above 100 psi. When hydrogen consumption ceases, flush the autoclave with nitrogen remove the catalyst by filtration. Evaporate the filtrate invacuo to give a residue. Dissolve the residue in ethyl acetate (5 L), acidify by the addition of 12M aqueous hydrochloric acid solution (150 mL), and heat to reflux for 15 minutes. Cool the mixture to 5° C. to give solid. Collect the solid by filtration, rinse with ethyl acetate, and air dry to give the title compound.

Workup

  1. customFlush the autoclave with nitrogen
  2. additioncharge with 255 psi of hydrogen
  3. temperatureto maintain the pressure above 100 psi
  4. customWhen hydrogen consumption ceases
  5. customflush the autoclave with nitrogen
  6. customremove the catalyst
  7. filtrationby filtration
  8. customEvaporate the filtrate invacuo
  9. customto give a residue
  10. temperatureheat
  11. temperatureto reflux for 15 minutes
  12. customto give solid
  13. customCollect the solid
  14. filtrationby filtration
  15. washrinse with ethyl acetate, and air
  16. customdry

Sources & evidence

ORD record
ord-e08d54e5568f4fa695a5860fc3216475
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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