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4-Bromo-1,2-dichlorobenzene → 1-(3,4-Dichloro-phenyl)-4-[4-(3-Piperidin-1-yl-propoxy)-phenyl]piperazine

HRID 1434584
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HRID 1434584 반응식
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:23][C:24]1[CH:25]=[C:26](Br)[CH:27]=[CH:28][C:29]=1[Cl:30].CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:23][C:24]1[CH:25]=[C:26]([N:20]2[CH2:19][CH2:18][N:17]([C:14]3[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:12][CH:13]=3)[CH2:22][CH2:21]2)[CH:27]=[CH:28][C:29]=1[Cl:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 634876Binap, (A+-)-HCID 99240131-[4-(3-Piperidin-1-ylpropoxy)phenyl]piperazineHCID 23676156Sodium t-butoxide

생성물 1

HCID 579357441-(3,4-Dichloro-phenyl)-4-[4-(3-Piperidin-1-yl-propoxy)-phenyl]piperazine

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 8857Ethyl Acetate용매

실험 절차

Tris(dibenzylidineacetone) di palladium (0) (5 mol %; 23 mg) was added to a mixture of 1-[4-(3-piperidin-1-yl-propoxy)-phenyl]-piperazine (D11) (150 mg; 0.49 mmol), 3,4-dichloro bromo benzene (160 mg; 1.2 eq), sodium tert-butoxide (71 mg; 1.1 eq) and racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (7.5 mol %; 24 mg) in dry toluene (3 ml). The resulting mixture was heated at reflux under argon for 18 hours. The reaction was allowed to cool to room temperature and diluted with ethyl acetate (10 ml). The resulting solids were removed by filtration and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica eluting with 3% methanol in dichloromethane to afford the title compound as a buff solid (45 mg)

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under argon for 18 hours
  3. customThe resulting solids were removed by filtration
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica eluting with 3% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-d0f9f1e5b5ed42eabc20fea828ac68be
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07615550B2

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