Réaction #85866

Équation de réaction

HBr

ethyl 1-(4-aminophenyl)piperidine-4-carboxylate

NaNO2

HBr

→

crude title compound

1-(4-bromophenyl)piperidine-4-carboxylic acid

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe resulting mixture was stirred
2. 2
   Températurerefluxed for 2 hours
3. 3
   AutreThe suspension thus obtained
4. 4
   Autrewas partitioned between 2N NaOH and ethyl acetate
5. 5
   LavageThe organic layer was washed with aqueous NaCl
6. 6
   Séchagedried over Na2SO4
7. 7
   Concentrationconcentrated

Mode opératoire

To a solution of ethyl 1-(4-aminophenyl)piperidine-4-carboxylate (2.48 g, 10 mmol) in 40 mL of HBr 40%, a solution of NaNO2 (0.69 g, 10 mmol) in 7 mL of water was slowly added at 0° C. The mixture was stirred for 15 minutes and added to a solution of CuBr (0.79 g, 5.5 mmol) in 30 mL of HBr 40%. The resulting mixture was stirred and refluxed for 2 hours. The suspension thus obtained was partitioned between 2N NaOH and ethyl acetate. The organic layer was washed with aqueous NaCl, dried over Na2SO4 and concentrated to afford crude title compound 1.56 g. MS (m/z): 286 (M+2)+

Source