تفاعل #48589

معادلة التفاعل

3,4-Dinitrofluorobenzene

4-hydroxy-1-methylpiperidine

sodium hydride

→

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

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added in several small portions
2. 2
   أخرىpartitioned between ethyl acetate and water
3. 3
   غسيلthe organic phase washed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   غسيلeluting with 5% MeOH/DCM

الإجراء التجريبي

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).

المصدر