تفاعل #2336524

معادلة التفاعل

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

المردود 51.6%

المذيبات

tert-butanol

ظروف التفاعل

المعالجة

1. 1
   أخرىSynthesis of this compound
2. 2
   درجة الحرارةthe mixture was heated on a steam bath for 3 h
3. 3
   أخرىpartitioned between ether and water
4. 4
   استخلاصThe organic phase was extracted with cold dilute HCl
5. 5
   استخلاصthe acidic aqueous phase was extracted with ether twice
6. 6
   استخلاصextracted with ether
7. 7
   غسيلThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   أخرىdried
9. 9
   أخرىevaporated under vacuum

الإجراء التجريبي

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.

المصدر