Реакция #2336524

Уравнение реакции

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

Выход 51.6%

Растворители

tert-butanol

Условия реакции

Обработка

1. 1
   ДругоеSynthesis of this compound
2. 2
   Температураthe mixture was heated on a steam bath for 3 h
3. 3
   Другоеpartitioned between ether and water
4. 4
   ЭкстракцияThe organic phase was extracted with cold dilute HCl
5. 5
   Экстракцияthe acidic aqueous phase was extracted with ether twice
6. 6
   Экстракцияextracted with ether
7. 7
   ПромывкаThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   Другоеdried
9. 9
   Другоеevaporated under vacuum

Методика

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.

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