Reaktion #85866

Reaktionsgleichung

HBr

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

NaNO2

HBr

→

crude title compound

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

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred
2. 2
   Temperaturrefluxed for 2 hours
3. 3
   SonstigeThe suspension thus obtained
4. 4
   Sonstigewas partitioned between 2N NaOH and ethyl acetate
5. 5
   WaschenThe organic layer was washed with aqueous NaCl
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated

Vorschrift

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)+

Quelle