Reacción #85866

Ecuación de reacción

HBr

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

NaNO2

HBr

→

crude title compound

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

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe resulting mixture was stirred
2. 2
   Temperaturarefluxed for 2 hours
3. 3
   OtroThe suspension thus obtained
4. 4
   Otrowas partitioned between 2N NaOH and ethyl acetate
5. 5
   LavadoThe organic layer was washed with aqueous NaCl
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated

Procedimiento

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)+

Fuente