Ethanol → 4-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide

HRID 400063Notes

Reaction equation

HRID 400063 reaction equation
Cl.C([N:9]1[CH2:14][CH2:13][C:12]([C:21]#[N:22])([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1.[OH-].[Na+].C([OH:27])C.OO>O.C(OCC)(=O)C.CO>[N:18]1[CH:19]=[CH:20][C:15]([C:12]2([C:21]([NH2:22])=[O:27])[CH2:13][CH2:14][NH:9][CH2:10][CH2:11]2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 189451181-Benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride

Product 1

HCID 544701184-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Alternately, combine 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride (20.3 g, 58 mmol), a concentrated aqueous sodium hydroxide solution (20 mL, 50%) and ethanol (400 mL). Heat to about 50° C. Add an aqueous solution of hydrogen peroxide (40 mL, 30%) over about 10 minutes. After 18 hours, add an aqueous solution of hydrogen peroxide (10 mL). After 3 hour, cool to ambient temperature and dilute with water (200 mL), concentrate in vacuo to remove most to the ethanol (about 400 mL). Add water (200 mL) and extract twice with ethyl acetate. Extract the combined organic layers with water and then brine, dry over MgSO4, filter, and evaporate in vacuo to give a solid. Dissolve the residue in hot ethyl acetate (500 mL) by the addition of methanol. Filter and concentrate the filtrate in vacuo to give a solid. Triturate the solid with dichloromethane and collect by filtration, and dry to give 1-benzyl-(4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide: Rf =0.62 (silica gel, 7/3 dichloromethane/methanol).

Workup

  1. waitAfter 3 hour
  2. temperaturecool to ambient temperature
  3. concentrationconcentrate in vacuo
  4. customto remove most to the ethanol (about 400 mL)
  5. extractionAdd water (200 mL) and extract twice with ethyl acetate
  6. extractionExtract the combined organic layers with water
  7. dry with materialbrine, dry over MgSO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a solid
  11. filtrationFilter
  12. concentrationconcentrate the filtrate in vacuo
  13. customto give a solid
  14. customTriturate the solid with dichloromethane
  15. filtrationcollect by filtration
  16. customdry

Sources & evidence

ORD record
ord-f3d3292d36e745bb8eaa027be42276a4
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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