Tetrahydrofuran → 1-[2-(Trimethylsilyl)ethylcarbonyl]-4-(4-nitrophenyl)piperazine

HRID 1007125ノート

反応式

HRID 1007125 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)(OC1C=CC([N+]([O-])=O)=CC=1)O[CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21].[O:35]1CCC[CH2:36]1>>[CH3:23][Si:20]([CH3:21])([CH3:22])[CH2:19][CH2:18][C:36]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:35]

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 804471-(4-Nitrophenyl)piperazineHCID 30861164-Nitrophenyl 2-(trimethylsilyl)ethyl carbonate

生成物 1

HCID 226677981-[2-(Trimethylsilyl)ethylcarbonyl]-4-(4-nitrophenyl)piperazine収率 71%

実験手順

A solution of 1-(4-nitrophenyl)piperazine (10 g, 48.31 mmol) and 2-(trimethylsilyl)ethyl p-nitrophenyl carbonate (14.4 g, 50.73 mmol) in tetrahydrofuran (220 mL) is refluxed for 3 hours with magnetic stirring and then stirred for 20 hours at room temperature. The reaction mixture is concentrated, the residue is taken up in dichloromethane and the organic phase is washed 4 times with 1N sodium hydroxide and twice with water. The organic phase is then dried over sodium sulphate, filtered and concentrated; the oily residue obtained is used without further purification in the following step (12 g, yield: 71%). 1H NMR (300 MHz, δ ppm) CDCl3: 0.04 (s, 9H), 1.02 (m, 2H), 3.43 (m, 4H), 3.65 (m, 4H), 4.22 (m, 2H), 6.82 (d, 2H), 8.13 (d, 2H).

後処理

  1. stirringstirred for 20 hours at room temperature
  2. concentrationThe reaction mixture is concentrated
  3. washthe organic phase is washed 4 times with 1N sodium hydroxide
  4. dry with materialThe organic phase is then dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe oily residue obtained
  8. customis used without further purification in the following step (12 g, yield: 71%)

出典と根拠

ORDレコード
ord-6f99f1947b24468884407db31391d5b9
出典データセット
uspto-grants-2004_09
特許番号
US06794382B2

反応ノート

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