Hydrochloric Acid → 1-Benzyl-3-methyl-4-piperidone

HRID 1865284Notes

Reaction equation

HRID 1865284 reaction equation
C(O[C:4]([C:6]1(C)[C:11](=[O:12])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)=O)C.Cl>>[CH2:13]([N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH:6]([CH3:4])[CH2:7]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 14666544Ethyl 1-benzyl-3-methyl-4-oxopiperidine-3-carboxylate

Product 1

HCID 5609651-Benzyl-3-methyl-4-piperidoneYield 76.2%

Conditions

Temperature
100 °C

Procedure

Ethyl-1-benzyl-3-methyl-4-oxo-piperidine-3-carboxylate (85 g, 0.31 mol) was dissolved in conc HCl (82 ml, 0.77 mol) and the reaction mixture was heated to 100° C. for 32 hrs. Solvent was removed under reduced pressure and the resulting solid was dissolved in the 300 ml CHCl3 and 400 ml pet ether was added to this under stirring to provide a solid. The solid was filter and was dissolved in 400 ml ethyl acetate and organic layer was washed with 10% NaOH aqueous solution. Layers were separated and concentration of organic layer afforded 48 g (75%) oil as a titled product.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe resulting solid was dissolved in the 300 ml CHCl3 and 400 ml pet ether
  3. additionwas added to
  4. customto provide a solid
  5. filtrationThe solid was filter
  6. dissolutionwas dissolved in 400 ml ethyl acetate
  7. washorganic layer was washed with 10% NaOH aqueous solution
  8. customLayers were separated

Sources & evidence

ORD record
ord-ff248cbb1076495bb610212b5d89a30c
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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