1-Iodo-3-nitrobenzene → Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate

HRID 1267113노트

반응식

HRID 1267113 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O1CCOCC1.CCOCC.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:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

8

반응물 4

HCID 125741-Iodo-3-nitrobenzeneHCID 80271Tri-o-tolylphosphineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 23676156Sodium t-butoxide

생성물 1

HCID 22330126Tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate수율 54%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 1-iodo-3-nitro-benzene (9 g), piperazine-1-carboxylic acid tert-butyl ester (13.5 g) and sodium tert-butoxide (9.7 g) in dioxane (150 mL) was added tris(dibenzylideneacetone)dipalladium (2 g) and tri-o-tolylphosphine (2.2 g) and the mixture was heated at reflux for 24 hours. The solution was then cooled to room temperature, taken in Et2O and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized from diisopropyl ether to give the title compound (6 g) as a yellow solid.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 hours
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was recrystallized from diisopropyl ether

출처 및 근거

ORD 기록
ord-3e6f4f4adc4544aa9e6884a8a24e610d
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552022B1

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