반응 #413140

반응 방정식

1-(2,2,2-trichloroethoxycarbonyl)-4-(2-naphthalenyloxy)piperidine

→

4-(2-naphthalenyloxy)piperidine

용매

acetic acid

tetrahydrofuran

water

반응 조건

후처리

1. 1
   기타the exothermic reaction
2. 2
   기타2 hours
3. 3
   여과The mixture is filtered
4. 4
   기타the solvents are removed in vacuo
5. 5
   기타The residue is partitioned between ether and aqueous sodium hydroxide
6. 6
   세척the organic phase washed with water
7. 7
   추출extracted with dilute aqueous hydrochloric acid
8. 8
   세척The acid extracts are washed with ether
9. 9
   추출extracted into ether and toluene
10. 10
    세척the organic solution washed
11. 11
    건조dried over magnesium sulfate
12. 12
    농축concentrated in vacuo

실험 절차

The resulting 1-(2,2,2-trichloroethoxycarbonyl)-4-(2-naphthalenyloxy)piperidine is dissolved in a mixture of 250 ml of acetic acid, 250 ml of tetrahydrofuran and 125 ml of water. 28.5 g (0.436 mole) of zinc dust is added in portions with stirring and the exothermic reaction allowed to proceed for 21/2 hours. The mixture is filtered and the solvents are removed in vacuo. The residue is partitioned between ether and aqueous sodium hydroxide and the organic phase washed with water and extracted with dilute aqueous hydrochloric acid. The acid extracts are washed with ether, made basic with sodium hydroxide and extracted into ether and toluene and the organic solution washed, dried over magnesium sulfate and concentrated in vacuo to yield 4-(2-naphthalenyloxy)piperidine, which is redissolved in ethanol/ether and treated with dry HCl, and the hydrochloride salt recrystallized from butanone/methanol. M.P. 229.5°-231.5° C.

출처