Reaktion #2133218

Reaktionsgleichung

product

4-n-Octyliodobenzene

product

tert-Butyl 4-(benzoyloxy)piperazine-1-carboxylate

→

title compound

Ausbeute 31.4%

tert-Butyl 4-(4-octylphenyl)piperazine-1-carboxylate

Ausbeute 31.4%

Lösungsmittel

Et2O

THF

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 30 min on ice-bath under N2
2. 2
   Temperaturto warm up to room temperature
3. 3
   workup.STIRRINGstirred for additional 10 min
4. 4
   Waschenwashed with 5% NaHCO3, H2O, brine
5. 5
   Trocknendried over anhydrous MgSO4
6. 6
   Filtrationfiltered
7. 7
   SonstigeThe filtrate was evaporated under reduced pressure
8. 8
   Sonstigethe residue was purified by FCC (SiO2, hexane/EtOAc 9:1)

Vorschrift

To a solution of the product of Step A (0.32 g; 1.01 mmol) in anhydrous THF (2 ml) 2 M iPrMgCl in THF (0.56 ml; 1.11 mmol) was added at −15° C. under N2, followed 1.27 M solution of anhydrous ZnCl2 in THF (0.41 ml; 0.52 mmol), after stirring for 1 h at 0° C. The resulting mixture was stirred for 30 min on ice-bath under N2 and the solution of the product of Step B (0.16 g; 0.51 mmol) and CuCl2 (2.5 mol %) in anhydrous THF (10 ml) was added. The resulting mixture was allowed to warm up to room temperature and stirred for additional 10 min. This was diluted to 20 ml with Et2O and washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc 9:1) to give the title compound (0.06 g; 31%), as a creamy syrup. 1H-NMR (CDCl3) 7.07 (d, 2H, J=8.6 Hz); 6.84 (d, 2H, J=8.6 Hz); 3.55 (t, 4H, J=5 Hz); 3.06 (t, 4H, J=5 Hz); 2.51 (t, 2H, J=7.94 Hz); 1.55-1.38 (m, 11H); 1.26 (m, 10H); 0.86 (t, 3H, J=6.93 Hz).

Quelle