Sulfuric Acid → Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate

HRID 1088352Notes

Reaction equation

HRID 1088352 reaction equation
C[O:2][C:3]1(OC)[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:4]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.S(=O)(=O)(O)O>O>[O:2]=[C:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH:4]1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 3019743Ethyl 3-(benzyloxy)-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 3019711Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 94 parts of ethyl 4,4-dimethoxy-3-(phenylmethoxy)-1-piperidinecarboxylate and 2300 parts of a sulfuric acid solution 1% in water was stirred and refluxed for 2.50 hours. The reaction mixture was cooled and the product was extracted three times with dichloromethane. The combined extracts were washed with a small amount of water, dried, filtered and evaporated. The residue was taken up in methylbenzene and the latter was evaporated again. The residue was stirred in petroleum ether. The latter was separated and the solvent was evaporated, yielding 64.9 parts of ethyl 4-oxo-3-(phenylmethoxy)-1-piperidinecarboxylate as a residue (intermediate 50).

Workup

  1. temperaturerefluxed for 2.50 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe product was extracted three times with dichloromethane
  4. washThe combined extracts were washed with a small amount of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customthe latter was evaporated again
  9. stirringThe residue was stirred in petroleum ether
  10. customThe latter was separated
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d4c82bf49a374db8acca0e07991709fc
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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