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

HRID 400062Notes

Reaction equation

HRID 400062 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>[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

6

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 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Combine 1-benzyl-4-cyano-4-(pyridin-4-yl)-piperidine hydrochloride (1.6 g, 4.5 mmol), a concentrated aqueous sodium hydroxide solution (1.5 mL, 50%, 9 mmol) and ethanol (30 mL). Heat to about 55° C. Add an aqueous solution of hydrogen peroxide (3.0 mL, 30%, 26 mmol) over about 10 minutes. After 3 hours, add an aqueous solution of hydrogen peroxide (2.0 mL). After 1 hour, cool to ambient temperature and dilute with water (20 mL), concentrate in vacuo, add water (40 mL), and again concentrate in vacuo to give a solid. Collect the solid by filtration, rinse with water, and dry to give 1-benzyl-(4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide: Rf =0.20 (silica gel, 9/1 dichloromethane/methanol).

Workup

  1. waitAfter 1 hour
  2. temperaturecool to ambient temperature
  3. concentrationconcentrate in vacuo
  4. additionadd water (40 mL)
  5. concentrationagain concentrate in vacuo
  6. customto give a solid
  7. customCollect the solid
  8. filtrationby filtration
  9. washrinse with water
  10. customdry

Sources & evidence

ORD record
ord-33ab0439849c4a97b2025c73928a9650
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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