Реакция #85866

Уравнение реакции

HBr

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

NaNO2

HBr

→

crude title compound

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

Растворители

water

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe resulting mixture was stirred
2. 2
   Температураrefluxed for 2 hours
3. 3
   ДругоеThe suspension thus obtained
4. 4
   Другоеwas partitioned between 2N NaOH and ethyl acetate
5. 5
   ПромывкаThe organic layer was washed with aqueous NaCl
6. 6
   Сушкаdried over Na2SO4
7. 7
   Концентрированиеconcentrated

Методика

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)+

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