Acetamide, N-(4-fluoro-3-nitrophenyl)- → N-{3-Nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

HRID 1435405ノート

反応式

HRID 1435405 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.F[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21]>CCO>[N+:20]([C:11]1[CH:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[CH:14]=[CH:15][C:10]=1[NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)([O-:22])=[O:21]

参加物

4

反応物 2

HCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-HCID 27732104-Aminomethyltetrahydropyran

生成物 1

HCID 57937362N-{3-Nitro-4-[(tetrahydro-2H-pyran-4-ylmethyl)amino]phenyl}acetamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Aminomethyl tetrahydropyran (13.7 g, 0.119 mol) was added to a solution of N-(4-Fluoro-3-nitrophenyl)acetamide (20.2 g, 0.102 mol) and TEA (20.9 mL, 15.2 g, 0.15 mol) in EtOH (350 mL). The reaction mixture was stirred overnight at reflux. The orange-red solid was collected by filtration, washed with water and dried in vacuo. The filtrate was concentrated. The residue was dissolved in EtOAc, washed with H2O, brine and dried over anhydrous Na2SO4. The crude product was purified by silica gel flash chromatography using EtOAc as eluent. Total yield: 28.9 g (97%). 1H NMR (400 MHz, CHLOROFORM-D) δ 1.4 (m, 2 H), 1.7 (m, 2 H), 1.89-2.00 (m, 1 H), 2.18 (s, 3 H), 3.22 (dd, J=6.44, 5.66 Hz, 2 H), 3.42 (dt, J=11.86, 2.05 Hz, 2 H), 4.02 (dd, J=10.94, 3.71 Hz, 2 H), 6.84 (d, J=9.37 Hz, 1 H), 7.20 (br.s, 1 H), 7.81 (dd, J=9.37, 2.54 Hz, 1 H), 8.09 (d, J=2.54 Hz, 1 H), 8.10-8.12 (m, 1 H).

後処理

  1. temperatureat reflux
  2. filtrationThe orange-red solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo
  5. concentrationThe filtrate was concentrated
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with H2O, brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe crude product was purified by silica gel flash chromatography

出典と根拠

ORDレコード
ord-51cc8f4f0ef6492a8badc422aa5f0f25
出典データセット
uspto-grants-2009_11
特許番号
US07615642B2

反応ノート

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