Toluene → 1-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine

HRID 1042656노트

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HRID 1042656 반응식
I[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CC(C)([O-])C.[Na+].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.[Pd].C(OCC)(=O)C.O>[CH3:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[CH2:18][CH2:17]1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 531671-MethylpiperazineHCID 108529273-Iodo-5-nitrobenzotrifluorideHCID 23676156Sodium t-butoxide

생성물 1

HCID 594280371-Methyl-4-(3-nitro-5-(trifluoromethyl)phenyl)piperazine

시약·촉매·용매 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

Into a 50 mL round bottom flask was placed the 1-iodo-3-nitro-5-(trifluoromethyl)benzene (1 g, 3.15 mmol), N-methylpiperazine (0.379 g, 3.78 mmol), bis(dibenzylideneacetone)palladium (0.029 g, 0.0315 mmol), sodium tert-butoxide (0.424 g, 4.416 mmol), 2-dicyclohexyl-2′-(N,N-dimethylamino)biphenyl (0.037 g, 0.094 mmol), and toluene (25 mL). Reaction was heated to 80° C. with stirring for 20 hours. Reaction was cooled to room temperature and water (1 mL) and ethyl acetate (10 mL) were added. The organic layer is separated, concentrated under reduced pressure and purified via silica column eluting with 0 to 20% methanol in dichloromethane. The title compound was obtained as an orange oil.

후처리

  1. customInto a 50 mL round bottom flask was placed
  2. customReaction
  3. customReaction
  4. temperaturewas cooled to room temperature
  5. customThe organic layer is separated
  6. concentrationconcentrated under reduced pressure
  7. custompurified via silica column
  8. washeluting with 0 to 20% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-05352d0948a740f5800074be52f9c0d5
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557996B2

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