Reaktion #48589

Reaktionsgleichung

3,4-Dinitrofluorobenzene

4-hydroxy-1-methylpiperidine

sodium hydride

→

4-(3,4-dinitro-phenoxy)-1-methyl-piperidine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added in several small portions
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   Waschenthe organic phase washed with brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Wascheneluting with 5% MeOH/DCM

Vorschrift

3,4-Dinitrofluorobenzene (1.86 g, 10 mmol) and 4-hydroxy-1-methylpiperidine (1.38 g, 12 mmol) were dissolved in THF (20 ml) and stirred at ambient temperature while sodium hydride (60% dispersion in mineral oil, 0.40 g, 10 mmol) was added in several small portions. The reaction mixture was stirred for one hour and then reduced in vacuo, partitioned between ethyl acetate and water, and the organic phase washed with brine, dried (MgSO4) and reduced in vacuo. The resulting residue was subject to column chromatography, eluting with 5% MeOH/DCM to give a yellow solid (1.76 g, 2:1 ratio of 4-(3,4-dinitro-phenoxy)-1-methyl-piperidine and a 4-(4-fluoro-2-nitro-phenoxy)-1-methyl-piperidine).

Quelle