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

HRID 1042656ノート

反応式

HRID 1042656 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05352d0948a740f5800074be52f9c0d5
出典データセット
uspto-grants-2013_10
特許番号
US08557996B2

反応ノート

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