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

HRID 1435405노트

반응식

HRID 1435405 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-51cc8f4f0ef6492a8badc422aa5f0f25
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615642B2

반응 노트

불러오는 중…