反応 #2336524

反応方程式

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

収率 51.6%

溶媒

tert-butanol

反応条件

後処理

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

実験手順

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.

出典