반응 #7502

반응 방정식

1-(phenylmethyl)-4-piperidinone

1-phenylethyl-1H-imidazole

Butyllithium

hexane

→

4-[1-(2-phenylethyl)-1H-imidazol-2-yl]-1-(phenylmethyl)-4-piperidinol

수율 75.0%

용매

H2O

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at −70° C. for 15 min
2. 2
   workup.ADDITIONwas added dropwise at a temperature below −55° C
3. 3
   workup.STIRRINGThe mixture was stirred at −70° C. for 1 hour
4. 4
   workup.ADDITIONwas added dropwise at a temperature below −55° C
5. 5
   workup.STIRRINGThe mixture was stirred at −70° C. for 1 hour
6. 6
   기타brought to room temperature
7. 7
   workup.STIRRINGstirred at room temperature overnight
8. 8
   기타The organic solvent was evaporated
9. 9
   농축The aqueous concentrate
10. 10
    추출was extracted with CH2Cl2
11. 11
    기타The organic layer was separated
12. 12
    건조dried (MgSO4)
13. 13
    여과filtered
14. 14
    기타the solvent was evaporated
15. 15
    기타The residue was crystallized from DIPE (1100 ml)
16. 16
    여과The precipitate was filtered off
17. 17
    세척washed with DIPE
18. 18
    기타dried

실험 절차

A mixture of DIPA (1.4 mol) in THF (3000 ml) was stirred at −70° C. under N2 flow. Butyllithium 2.5 M/hexane (1.3 mol) was added portionwise at a temperature below −40° C. The mixture was stirred at −70° C. for 15 min. 1-phenylethyl-1H-imidazole (1 mol) dissolved in THF was added dropwise at a temperature below −55° C. The mixture was stirred at −70° C. for 1 hour. 1-(phenylmethyl)-4-piperidinone (1.2 mol) dissolved in THF was added dropwise at a temperature below −55° C. The mixture was stirred at −70° C. for 1 hour, then brought to room temperature, stirred at room temperature overnight and decomposed with H2O. The organic solvent was evaporated. The aqueous concentrate was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was crystallized from DIPE (1100 ml). The precipitate was filtered off, washed with DIPE and dried, yielding 271 g of 4-[1-(2-phenylethyl)-1H-imidazol-2-yl]-1-(phenylmethyl)-4-piperidinol (75%) (interm. 1).

출처