Acetamide, N-(4-fluoro-3-nitrophenyl)- → N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)acetamide

HRID 1435487노트

반응식

HRID 1435487 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.[F:16][C:17]1([F:25])[CH2:22][CH2:21][CH:20]([CH2:23][NH2:24])[CH2:19][CH2:18]1>CCO>[F:16][C:17]1([F:25])[CH2:22][CH2:21][CH:20]([CH2:23][NH:24][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:19][CH2:18]1

참가 물질

4

반응물 2

HCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-HCID 451589311-(4,4-Difluorocyclohexyl)methanamine hydrochloride

생성물 1

HCID 57441084N-(4-{[(4,4-Difluorocyclohexyl)methyl]amino}-3-nitrophenyl)acetamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

N-(4-Fluoro-3-nitrophenyl)acetamide (1.15 g, 5.84 mmol) and [(4,4-difluorocyclohexyl)methyl]amine hydrochloride (1.30 g, 7.59 mmol) were stirred in 30 mL of EtOH containing TEA (2.40 mL, 17.5 mmol) at 80° C. for 48 h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous 5% KHSO4 solution, saturated aqueous NaHCO3 solution, saturated aqueous NaCl solution and dried over anhydrous Na2SO4. The product was crystallized from EtOAc. The left over mother liquor was purified by flash chromatography on silica gel using hexane/acetone (2:1) as eluent. Yield: 1.50 g (78%); 1H NMR (400 MHz, CDCl3) δ 1.33-1.47 (m, 2 H), 1.66-1.77 (m, 2 H), 1.77-1.86 (m, 1 H), 1.89-1.93 (m, 1 H), 1.93-1.97 (m, 1 H), 2.10-2.17 (m, 2 H), 2.18 (s, 3 H), 3.23 (dd, J=6.74, 5.76 Hz, 2 H), 6.83 (d, J=9.37 Hz, 1 H), 7.15 (s, 1 H), 7.80 (dd, J=9.18, 2.54 Hz, 1 H), 8.09 (d, J=2.54 Hz, 2 H).

후처리

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with aqueous 5% KHSO4 solution, saturated aqueous NaHCO3 solution, saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe product was crystallized from EtOAc
  6. waitThe left over mother liquor
  7. customwas purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-816fd2d794ce41e4baa339af6fa5bdfc
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615642B2

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