تفاعل #85866

معادلة التفاعل

HBr

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

NaNO2

HBr

→

crude title compound

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

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred
2. 2
   درجة الحرارةrefluxed for 2 hours
3. 3
   أخرىThe suspension thus obtained
4. 4
   أخرىwas partitioned between 2N NaOH and ethyl acetate
5. 5
   غسيلThe organic layer was washed with aqueous NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

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)+

المصدر