Hydrochloric Acid → 4-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide hydrochloride

HRID 400064Notes

Reaction equation

HRID 400064 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C(O)C.[ClH:19].O1CCOCC1>[Pd].CO>[ClH:19].[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:13]([NH2:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 312751,4-DioxaneHCID 544701184-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide

Product 1

HCID 675621254-(Pyridin-4-yl)-piperidine-4-carboxylic acid amide hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine 1-benzyl-(4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide, (0.22 g, 0.67 mmol) and ethanol (20 mL). Add 5% palladium-on-carbon (0.14 g) and hydrogenate on a Parr apparatus at 55 psi. After 48 hours, remove the catalyst by filtration and evaporate the filtrate in vacuo to give a residue. Combine the residue and methanol. Add a solution of hydrochloric acid in dioxane (2 mL, 4M, 8 mmol) to give a solid. Collect the solid by filtration to give 4-(pyridin-4-yl)-piperidine-4-carboxylic acid amide hydrochloride.

Workup

  1. customremove the catalyst
  2. filtrationby filtration
  3. customevaporate the filtrate in vacuo
  4. customto give a residue
  5. customto give a solid
  6. customCollect the solid
  7. filtrationby filtration

Sources & evidence

ORD record
ord-91894978cfef4465bf1339c356b54b66
Source dataset
uspto-grants-1998_10
Patent number
US05824690

Reaction notes

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