1-Tert-butylpiperazine → 1-Phenylpiperazine

HRID 2297590노트

반응식

HRID 2297590 반응식
C(O[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1Br)CCC.C([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.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>[C:6]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 35305721-Tert-butylpiperazineHCID 190081261-Bromo-2-butoxybenzeneHCID 23676156Sodium t-butoxide

생성물 1

HCID 70961-Phenylpiperazine수율 157.1%

시약·촉매·용매 2

HCID 634876Binap, (A+-)-촉매HCID 1140Toluene용매

실험 절차

Part A: To a solution of n-butyloxybromobenzene (5.00 g, 21.82 mmol) in toluene (50 mL) was added tert-butyl piperazine (4.88 g, 26.18 mmol) and sodium tert-butoxide (2.94 g, 30.55 mmol). After stirring at ambient temperature for several minutes, BINAP (0.408 g, 0.655 mmol) and tris(dibenzyldeneacetone)-dipallidium (0) (0.200 g, 0.218 mmol) were added. The resulting mixture was heated to eighty degrees Celsius for 21 hours. After cooling to ambient temperature, the reaction mixture was filtered through a pad of Celite®, washing with diethyl ether and dichloromethane. Chromatography (on silica, ethyl acetate/hexanes) provided the phenyl-piperazine as a tan solid (5.56 g, 76%).

후처리

  1. temperatureThe resulting mixture was heated to eighty degrees Celsius for 21 hours
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe reaction mixture was filtered through a pad of Celite®
  4. washwashing with diethyl ether and dichloromethane

출처 및 근거

ORD 기록
ord-57d6173298034604bd9735ba369e20f5
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492367B1

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