Pyridine → Ethyl 1-benzoylpiperidine-4-carboxylate

HRID 1005440Notes

Reaction equation

HRID 1005440 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.N1C=CC=CC=1.C1(C)C=CC=CC=1.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:25]([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:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 7412Benzoyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateYield 100.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
9 °C

Procedure

To 157.21 g (1 mol) of ethyl isonipecotate (A) were added 79.10 g (1 mol) of pyridine and 1 l of toluene. After cooling the mixture to 9° C., thereto was added dropwise 147.6 g (1.05 mol) of benzoyl chloride at 10° to 20° C. over 30 minutes with cooling. The reaction mixture was further stirred with cooling with ice for 1 hour and at room temperature for 1 hour. Then, thereto was added 500 ml of water to separate an organic layer. The organic layer was washed with 100 ml of water and 200 ml of a 5% aqueous solution of sodium hydrogencarbonate, succesively. Then, thereto was added 10 g of anhydrous magnesium sulfate. After drying, the solvent was removed by distillation to obtain 262.48 g of ethyl N-benzoylisonipecotate (B). The NMR spectrum of the obtained compound was measured. The result is shown below.

Workup

  1. temperaturewith cooling
  2. temperaturewith cooling with ice for 1 hour and at room temperature for 1 hour
  3. customto separate an organic layer
  4. washThe organic layer was washed with 100 ml of water and 200 ml of a 5% aqueous solution of sodium hydrogencarbonate
  5. additionThen, thereto was added 10 g of anhydrous magnesium sulfate
  6. customAfter drying
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-d17ce14113584790aea12f33b97ecc98
Source dataset
uspto-grants-2000_04
Patent number
US06054586

Reaction notes

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