反应 #2336524

反应方程式

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

收率 51.6%

溶剂

tert-butanol

反应条件

后处理

1. 1
   其他Synthesis of this compound
2. 2
   温度the mixture was heated on a steam bath for 3 h
3. 3
   其他partitioned between ether and water
4. 4
   萃取The organic phase was extracted with cold dilute HCl
5. 5
   萃取the acidic aqueous phase was extracted with ether twice
6. 6
   萃取extracted with ether
7. 7
   洗涤The ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   其他dried
9. 9
   其他evaporated under vacuum

实验过程

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.

来源