Reaktion #7502

Reaktionsgleichung

1-(phenylmethyl)-4-piperidinone

1-phenylethyl-1H-imidazole

Butyllithium

hexane

→

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

Ausbeute 75.0%

Lösungsmittel

H2O

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

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
   Sonstigebrought to room temperature
7. 7
   workup.STIRRINGstirred at room temperature overnight
8. 8
   SonstigeThe organic solvent was evaporated
9. 9
   EinengenThe aqueous concentrate
10. 10
    Extraktionwas extracted with CH2Cl2
11. 11
    SonstigeThe organic layer was separated
12. 12
    Trocknendried (MgSO4)
13. 13
    Filtrationfiltered
14. 14
    Sonstigethe solvent was evaporated
15. 15
    SonstigeThe residue was crystallized from DIPE (1100 ml)
16. 16
    FiltrationThe precipitate was filtered off
17. 17
    Waschenwashed with DIPE
18. 18
    Sonstigedried

Vorschrift

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).

Quelle