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

HRID 415116

反応式

HRID 415116 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
50 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-db0ed36138b04b8ca6901f55354d3b4c
出典データセット
uspto-grants-2012_01
特許番号
US08088767B2

関連ノート

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