Hydrochloric Acid → Ethyl 2-oxopiperidine-4-carboxylate

HRID 62472Notes

Reaction equation

HRID 62472 reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][N:3]1C(OC(C)(C)C)=O.Cl>C(Cl)Cl.O1CCOCC1>[O:1]=[C:2]1[CH2:7][CH:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67300084HCID 67300084, compound

Product 1

HCID 18699051Ethyl 2-oxopiperidine-4-carboxylateYield 94.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the 1-tert-butyl 4-ethyl 2-oxopiperidine-1,4-dicarboxylate (20 g, 74.45 mmol) in DCM (93 mL) was add 4N hydrogen chloride in dioxane (30 mL). The reaction was stirred at room temperature for 1 hour and then the solvent was removed under reduced pressure. The resulting residue was dissolved in DCM and water, then adjusted to PH=8 with saturated aqueous Na2CO3 solution. The mixture was extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to afford ethyl 2-oxopiperidine-4-carboxylate (12 g, yield 94.5%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe resulting residue was dissolved in DCM
  3. extractionThe mixture was extracted with DCM
  4. washthe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-10e7c520627d43ecbbbb41bdaf3273a7
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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