Trifluoroacetic acid → Methyl 3-(piperazin-1-yl)benzoate

HRID 1157162노트

반응식

HRID 1157162 반응식
C(O[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=C[CH:20]=[C:19](Br)[CH:18]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:18]=[CH:19][CH:20]=[C:6]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:22]=1

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 12070Methyl 3-bromobenzoateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

생성물 1

HCID 18930727Methyl 3-(piperazin-1-yl)benzoate수율 52.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a mixture containing piperazine-1-carboxylic acid tert-butyl ester (400 mg, 2.16 mmol), 3-bromo-benzoic acid methyl ester (547 mg, 2.56 mmol), Pd(AcO) (32 mg, 0.14 mmol), 2-(di-t-butylphosphino)biphenyl (80 mg, 0.28 mmol) and sodium t-butoxide (400 mg, 4 mmol) in toluene (20 mL) was degassed with Ar. The reaction mixture was heated at 50 C for overnight. At the end of reaction, ethyl acetate was added and the mixture was filter through celite. After removal of solvent, TFA was added to the residue. The reaction mixture was stirred at ambient temperature for 1 hour. The excess TFA was removed under vacuum and the residue was purified using prep-HPLC to give desired product (250 mg, 37% yield for two steps) as TFA salt.

후처리

  1. customwas degassed with Ar
  2. temperatureThe reaction mixture was heated at 50 C for overnight
  3. customAt the end of reaction, ethyl acetate
  4. additionwas added
  5. filtrationthe mixture was filter through celite
  6. customAfter removal of solvent, TFA
  7. additionwas added to the residue
  8. customThe excess TFA was removed under vacuum
  9. customthe residue was purified

출처 및 근거

ORD 기록
ord-c0c3a34054e14a23b21b3756a377dcd7
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807672B2

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