Hydrochloric Acid → 1-(pyridin-3-ylmethyl)piperidin-4-one

HRID 972822Notes

Reaction equation

HRID 972822 reaction equation
[H-].[Na+].[Na].COC([CH2:8][CH2:9][N:10]([CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH2:11][CH2:12][C:13]([O:15]C)=O)=O.Cl>C1C=CC=CC=1>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][N:10]2[CH2:9][CH2:8][C:13](=[O:15])[CH2:12][CH2:11]2)[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydride2×HCID 5360545SodiumHCID 53766522HCID 53766522, compound

Product 1

HCID 64216241-(pyridin-3-ylmethyl)piperidin-4-oneYield 71.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

72 Grams of sodium hydride (50% dispersion in oil) were added to 1.5 liters of sodium dried benzene and the suspension formed was refluxed. 137.61 grams of 3-[N,N-di(2-methoxycarbonylethyl)aminomethyl]pyridine were added dropwise to the refluxing sodium hydride suspension in benzene and the solution was heated for a further 21/2 hours. 500 Milliliters of concentrated hydrochloric acid was added carefully. The mixture was filtered, separated and the acid layer combined with a further 200 milliliters of concentrated hydrochloric acid and refluxed for 18 hours. Solid sodium carbonate was added till the solution had a pH of 8. The mixture was filtered and the solution treated with benzene. The benzene extracts were combined, dried over magnesium sulphate and the solvent was evaporated to give 66.58 grams of N-(3-pyridylmethyl)-4-piperidone.

Workup

  1. customthe suspension formed
  2. temperaturewas refluxed
  3. temperaturethe solution was heated for a further 21/2 hours
  4. filtrationThe mixture was filtered
  5. customseparated
  6. temperaturerefluxed for 18 hours
  7. additionSolid sodium carbonate was added till the solution
  8. filtrationThe mixture was filtered
  9. additionthe solution treated with benzene
  10. dry with materialdried over magnesium sulphate
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3774ab3560d24718830e25fa546eaf61
Source dataset
uspto-grants-1977_10
Patent number
US04053615

Reaction notes

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