반응 #652809

반응 방정식

2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine

4-(4-chlorophenyl)-4-hydroxypiperidine

4-(4-chlorophenyl)-4-hydroxypiperidine

→

title compound

수율 28.4%

1-[(5-Amino-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl]-4-(4-chlorophenyl)-4-piperidinol

수율 28.4%

용매

xylene

반응 조건

후처리

1. 1
   온도refluxed for 16 hours
2. 2
   온도the mixture was refluxed for 24 hours
3. 3
   온도After cooling
4. 4
   여과the reaction mixture was filtered
5. 5
   세척washed with diethyl ether
6. 6
   추출The filtrate was extracted with 1N-hydrochloric acid
7. 7
   세척This aqueous layer was washed with diethyl ether
8. 8
   추출This solution was extracted with ethyl acetate
9. 9
   세척the organic layer was washed with saturated aqueous NaCl
10. 10
    건조dried over MgSO4
11. 11
    여과filtered
12. 12
    농축concentrated under reduced pressure
13. 13
    기타The residue was crystallized from diethyl ether/hexane

실험 절차

A suspension of 2-bromomethyl-2,3-dihydro-2,4,6,7-tetramethyl-5-benzofuranamine (1.4 g) and 4-(4-chlorophenyl)-4-hydroxypiperidine (1.3 g) in xylene (10 mL) was stirred under nitrogen gas at 120° C. for 1.5 hours and, then, refluxed for 16 hours. Thereafter, 0.85 g of 4-(4-chlorophenyl)-4-hydroxypiperidine was added and the mixture was refluxed for 24 hours. After cooling, the reaction mixture was filtered and washed with diethyl ether. The filtrate was extracted with 1N-hydrochloric acid and the aqueous layer was made weakly acidic with saturated aqueous sodium hydrogen carbonate (NaHCO3). This aqueous layer was washed with diethyl ether and made weakly basic with saturated aqueous NaHCO3. This solution was extracted with ethyl acetate and the organic layer was washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from diethyl ether/hexane to provide 0.58 g of the title compound. Yield 28%.

출처