تفاعل #69983

معادلة التفاعل

4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine

sodium tert-butoxide

ethyl acetate

3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

→

4-{4-[4-(pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

المردود 62.8%

المذيبات

o-xylene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONaddition
2. 2
   درجة الحرارةHeating
3. 3
   أخرىis brought back to ambient temperature
4. 4
   غسيلThe mixture is washed twice with water
5. 5
   تجفيفThe organic phase is dried over sodium sulphate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe crude product obtained
8. 8
   أخرىis chromatographed on silica gel, elution

الإجراء التجريبي

1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are placed in 20 ml of anhydrous o-xylene. 0.844 g of 3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester is added, then 0.519 g of sodium tert-butoxide is added, followed by 0.032 g of palladium acetate, and then addition is completed with 0.029 g of tri(tert-butyl)phosphine. The reaction mixture is heated at 150° C. for 6 h. Heating is subsequently halted, the mixture is brought back to ambient temperature and ethyl acetate is added. The mixture is washed twice with water and then twice with a saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a dichloromethane/methanol (99/1 to 97/3) mixture. 1.1 g of 4-{4-[4-(pyridin-4-yloxy)piperidin-1-yl]phenyl}-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained.

المصدر