Pyridine → Ethyl 1-benzoylpiperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence