Reacción #2336524

Ecuación de reacción

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

Rendimiento 51.6%

Disolventes

tert-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroSynthesis of this compound
2. 2
   Temperaturathe mixture was heated on a steam bath for 3 h
3. 3
   Otropartitioned between ether and water
4. 4
   ExtracciónThe organic phase was extracted with cold dilute HCl
5. 5
   Extracciónthe acidic aqueous phase was extracted with ether twice
6. 6
   Extracciónextracted with ether
7. 7
   LavadoThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   Otrodried
9. 9
   Otroevaporated under vacuum

Procedimiento

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.

Fuente