Toluene → 1-(Pyridin-3-yl)piperazine

HRID 564877

반응식

HRID 564877 반응식
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

참가 물질

8

반응물 4

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

생성물 1

HCID 4372341-(Pyridin-3-yl)piperazine수율 29%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c4240a151e8047849a417902692f5887
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06169086A

연결된 노트

불러오는 중…