Piperazine → 1-(3-Fluorophenyl)piperazine

HRID 459813

反応式

HRID 459813 の反応式
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 4837PiperazineHCID 140821-Bromo-3-fluorobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 774181-(3-Fluorophenyl)piperazine

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1 g (5.71 mmol) of 3-fluorobromobenzene and 2.95 g (34.29 mmol) of piperazine are dissolved in 20 ml of toluene, and 0.77 g (8 mmol) of sodium tert-butoxide is added. In the presence of 0.11 g (0.17 mmol) of BINAP and 0.05 g (0.06 mmol) of tris(dibenzylideneacetone)dipalladium, the mixture is then stirred under reflux overnight. After cooling, ethyl acetate is added and the mixture is washed with water. The mixture is then extracted with 1N hydrochloric acid, and the aqueous phase is washed with ethyl acetate. The pH is adjusted to 8–9 and the mixture is then extracted with dichloromethane. The organic phase is dried over magnesium sulphate and the solvent is removed, giving the target compound.

後処理

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. washthe mixture is washed with water
  4. extractionThe mixture is then extracted with 1N hydrochloric acid
  5. washthe aqueous phase is washed with ethyl acetate
  6. extractionthe mixture is then extracted with dichloromethane
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. customthe solvent is removed
  9. customgiving the target compound

出典と根拠

ORDレコード
ord-83ceb8398b0a4c5a9a0c9f3f58d2e4e7
出典データセット
uspto-grants-2007_03
特許番号
US07196086B2

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