Sodium hydride → 4-(3,4-Dinitrophenoxy)-1-methylpiperidine

HRID 132049

반응식

HRID 132049 반응식
[N+:1]([C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[OH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.[H-].[Na+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 2986753,4-Dinitrofluorobenzene

생성물 1

HCID 714182034-(3,4-Dinitrophenoxy)-1-methylpiperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  1. additionwas added in several small portions
  2. custompartitioned between ethyl acetate and water
  3. washthe organic phase washed with brine
  4. dry with materialdried (MgSO4)
  5. washeluting with 5% MeOH/DCM

출처 및 근거

ORD 기록
ord-b75698d51d834ba0b583897cfe0cd8f6
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07385059B2

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