Diisopropylethylamine → Tert-butyl 4-(3,4-dinitrophenyl)-3-methylpiperazine-1-carboxylate

HRID 415116

반응식

HRID 415116 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][CH:15]1[NH:20][CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16]1.C(N(C(C)C)CC)(C)C>CC(N(C)C)=O>[N+:11]([C:4]1[CH:3]=[C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH:15]2[CH3:14])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])([O-:13])=[O:12]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 2986753,4-DinitrofluorobenzeneHCID 2756810tert-Butyl 3-methylpiperazine-1-carboxylate

생성물 1

HCID 59349587Tert-butyl 4-(3,4-dinitrophenyl)-3-methylpiperazine-1-carboxylate

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
50 °C

실험 절차

4-Fluoro-1,2-dinitrobenzene (0.93 g, 5.0 mmol, commercially available from Oakwood Products) and tert-butyl 3-methylpiperazine-1-carboxylate (1.0 g, 5.0 mmol) were dissolved in 3 mL of DMA, and 3 mL of diisopropylethylamine was added. The mixture was stirred at 50° C. overnight, and then cooled to room temperature, separated between ethyl acetate and water. The combined organic were washed with water, brine, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated by silica gel column (20% to 40% ethyl acetate in hexanes) to give 1.0 g of tert-butyl 4-(3,4-dinitrophenyl)-3-methylpiperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3): δ 8.05 (d, 2H), 6.84 (m, 2H), 3.90-4.10 (m, 3H), 3.05-3.60 (m, 4H), 1.50 (s, 9H), 1.10 (s, 3H). MS (EI): 367 (MH+).

후처리

  1. temperaturecooled to room temperature
  2. customseparated between ethyl acetate and water
  3. washThe combined organic were washed with water, brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by silica gel column (20% to 40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-db0ed36138b04b8ca6901f55354d3b4c
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088767B2

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