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

HRID 659794

反応式

HRID 659794 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95b6aa0fa35146dfa68fd731ce5c6b4a
出典データセット
uspto-grants-2011_12
特許番号
US08080666B2

関連ノート

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