Reaktion #2336524

Reaktionsgleichung

4-hydroxypiperidine

p-methylbenzyl chloride

potassium carbonate

→

1-(4-methylbenzyl)-4-hydroxypiperidine

Ausbeute 51.6%

Lösungsmittel

tert-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSynthesis of this compound
2. 2
   Temperaturthe mixture was heated on a steam bath for 3 h
3. 3
   Sonstigepartitioned between ether and water
4. 4
   ExtraktionThe organic phase was extracted with cold dilute HCl
5. 5
   Extraktionthe acidic aqueous phase was extracted with ether twice
6. 6
   Extraktionextracted with ether
7. 7
   WaschenThe ether phase was washed with dilute aqueous sodium bicarbonate solution, brine
8. 8
   Sonstigedried
9. 9
   Sonstigeevaporated under vacuum

Vorschrift

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.

Quelle