Piperazine → 1-(2-Nitrophenyl)piperazine

HRID 278904

反応式

HRID 278904 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([O-:10])=[O:9]

参加物

3

反応物 2

HCID 4837PiperazineHCID 113411-Bromo-2-nitrobenzene

生成物 1

HCID 1009491-(2-Nitrophenyl)piperazine収率 92%

反応条件

温度
100 °C

実験手順

A heterogenous reaction mixture containing 2-bromo-nitrobenzene (2.02 g, 10.0 mmol) and piperazine (4.3 g, 50.0 mmol) was heated at 100° C. for 10 hours. The orange-red solid was extracted with ethyl acetate and washed thoroughly with 3 N NaOH solution followed by brine. The organic layer was separated and dried over Na2SO4, filtered and the solvent was removed in vacuo. The resulting red oil was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH) to yield 1-(2-nitrophenyl)-piperazine as an orange-red oil (1.90 g, 92%). It was characterized as a hydrochloride salt. Analysis calculated for C10H14N3O2Cl0.10 CHCl3: C, 47.46; H, 5.56; N, 16.44. Found: C, 47.63; H, 5.69; N. 16.42.

後処理

  1. extractionThe orange-red solid was extracted with ethyl acetate
  2. washwashed thoroughly with 3 N NaOH solution
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe resulting red oil was purified by column chromatography on silica gel (1:1 hexane/EtOAc followed by 4:1 EtOAc/MeOH)

出典と根拠

ORDレコード
ord-292e1c56c9ee4f56b870e2d0e13d33ac
出典データセット
uspto-grants-2002_03
特許番号
US06362182B1

関連ノート

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