Sodium Hydroxide → 1-(pyridin-3-ylmethyl)piperidin-4-amine

HRID 972823Notes

Reaction equation

HRID 972823 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:2]=1.Cl.O[NH3+:17].[OH-].[Na+].[Al]>C(O)C.[Ni]>[NH2:17][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 5359268AluminumHCID 64216241-(pyridin-3-ylmethyl)piperidin-4-oneHCID 22029257Hydroxyammonium hydrochloride

Product 1

HCID 64842041-(pyridin-3-ylmethyl)piperidin-4-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

38.05 Grams of N-(3-pyridylmethyl)-4-piperidone and 27.8 grams of hydroxylammonium hydrochloride were dissolved in 600 milliliters of ethanol. 300 milliliters of 30% sodium hydroxide were added and the solution refluxed for half an hour, and then 40 grams of nickel, aluminium alloy were carefully added portionwise to the refluxing solution. The solution was refluxed for a further 3 hours, cooled and filtered through kieselguhr. The solution was evaporated and the residue treated with ether. The combined ether extracts were dried over magnesium sulphate and evaporated to give 33.72 grams of 4-amino-N-(3-pyridylmethyl)piperidine.

Workup

  1. temperaturethe solution refluxed for half an hour
  2. temperatureThe solution was refluxed for a further 3 hours
  3. temperaturecooled
  4. filtrationfiltered through kieselguhr
  5. customThe solution was evaporated
  6. additionthe residue treated with ether
  7. dry with materialThe combined ether extracts were dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-18cfbd80d4a14d689f7f2743336793c5
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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