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

HRID 270764

반응식

HRID 270764 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 27375271-(2,4-Dichlorophenyl)piperazine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b76be913381d43bbaac68cb899eb6723
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449576B1

연결된 노트

불러오는 중…