Toluene → 1-(Pyridin-3-yl)piperazine

HRID 564877

反応式

HRID 564877 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>O.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].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:3]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 4837PiperazineHCID 122863-BromopyridineHCID 23676156Sodium t-butoxide

生成物 1

HCID 4372341-(Pyridin-3-yl)piperazine収率 29%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

実験手順

A mixture of 1.0 g (6.3 mmol) of 3-bromopyridine, 2.2 g (25 mmol) of piperazine, 16 mg of tris(dibenzylideneacetone)-dipalladium(0), 32 mg of (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1.3 g (13.4 mmol) of sodium t-butoxide, and 50 ml of toluene was heated under reflux for 24 hours in a nitrogen atmosphere. The reaction mixture was diluted with water and extracted with chloroform. The combined organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was evaporated off, and the residue was purified by silica gel column chromatography using a 9:1 mixture of chloroform and methanol as a developing solvent to give 0.27 g (29%) of the title compound.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours in a nitrogen atmosphere
  3. extractionextracted with chloroform
  4. washThe combined organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated off
  7. customthe residue was purified by silica gel column chromatography
  8. additiona 9:1 mixture of chloroform and methanol as a developing solvent

出典と根拠

ORDレコード
ord-c4240a151e8047849a417902692f5887
出典データセット
uspto-grants-2001_01
特許番号
US06169086A

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