Diethyl Ether → Ethyl 1-benzoylpiperidine-4-carboxylate

HRID 962729Notes

Reaction equation

HRID 962729 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.CCOCC.C(=O)([O-])[O-].[Na+].[Na+].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C.O>[C:23]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a ice cold, stirred mixture of 55 g of ethyl isonipecotate, 200 mL of ether, 200 mL of saturated sodium carbonate and 200 mL of water was added dropwise 40 mL of benzoyl chloride. The resulting mixture was allowed to warm and stir overnight, diluted with 200 mL of ethyl acetate and separated. The organic layer was washed with 200 mL of 1N hydrochloric acid, dried over MgSO4, and concentrated. Drying the residue under vacuum gave 83.3 g (92%) of ethyl 1-benzoyl-4-piperidinecarboxylate as a white solid.

Workup

  1. temperatureto warm
  2. customseparated
  3. washThe organic layer was washed with 200 mL of 1N hydrochloric acid
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customDrying the residue under vacuum

Sources & evidence

ORD record
ord-d65b9e2e83804b12b1091a73126a5e22
Source dataset
uspto-grants-1998_06
Patent number
US05760054

Reaction notes

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