Piperazine → 1-(2,4-Dichlorophenyl)piperazine

HRID 270764

反応式

HRID 270764 の反応式
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].[NH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.[Cl:59][C:60]1[CH:65]=[C:64]([Cl:66])[CH:63]=[CH:62][C:61]=1Br>C1COCC1>[Cl:59][C:60]1[CH:65]=[C:64]([Cl:66])[CH:63]=[CH:62][C:61]=1[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1

参加物

6

反応物 4

HCID 4837PiperazineHCID 709471-Bromo-2,4-dichlorobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

生成物 1

HCID 27375271-(2,4-Dichlorophenyl)piperazine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

BINAP (219 mg), Pd(II) acetate (397 mg, 0.176 mmol), tBuONa (1.19 g, 12.3 mmol), piperazine (837 mg, 9.73 mmol) and THF (40 mL) were mixed together and stirred at room temperature for 30 min under nitrogen atmosphere. 2,4-dichlorobromobenzene (2 g, 8.84 mmol) in THF (10 mL) was added to the mixture drop wise and heated at 70° C. for 14 h. Excess THF was then evaporated and extracted with ethyl acetate. The crude product was obtained on concentration of the ethyl acetate layer after washing with brine and drying. Flash chromatography on silica gel eluting with 2% MeOH in CHCl3 gave 1-(2,4-Dichloro-phenyl)-piperazine.

後処理

  1. temperatureheated at 70° C. for 14 h
  2. customExcess THF was then evaporated
  3. extractionextracted with ethyl acetate
  4. customThe crude product was obtained on concentration of the ethyl acetate layer
  5. washafter washing with brine
  6. customdrying

出典と根拠

ORDレコード
ord-b76be913381d43bbaac68cb899eb6723
出典データセット
uspto-grants-2008_11
特許番号
US07449576B1

関連ノート

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