반응 #2336524

반응 방정식

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

수율 51.6%

용매

tert-butanol

반응 조건

후처리

1. 1
   기타Synthesis of this compound
2. 2
   온도the mixture was heated on a steam bath for 3 h
3. 3
   기타partitioned between ether and water
4. 4
   추출The organic phase was extracted with cold dilute HCl
5. 5
   추출the acidic aqueous phase was extracted with ether twice
6. 6
   추출extracted with ether
7. 7
   세척The ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   기타dried
9. 9
   기타evaporated under vacuum

실험 절차

Synthesis of this compound was accomplished according to Scheme 33. To 5.05 g (50 mmol) of 4-hydroxypiperidine and 7.08 g (50 mmol) of p-methylbenzyl chloride in 25 mL of tert-butanol was added excess solid potassium carbonate, and the mixture was heated on a steam bath for 3 h. The mixture was cooled to room temperature and partitioned between ether and water. The organic phase was extracted with cold dilute HCl, and the acidic aqueous phase was extracted with ether twice. The aqueous phase was made basic with ice and 50% aqueous NaOH and extracted with ether. The ether phase was washed with dilute aqueous sodium bicarbonate solution, brine, dried, and evaporated under vacuum to give 5.3 g (52) of 1-(4-methylbenzyl)-4-hydroxypiperidine (123) as an oil. GC/MS showed 100% purity with a molecular ion of 205.

출처