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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
Notes
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Reaction equation

HRID 1434584 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-d0f9f1e5b5ed42eabc20fea828ac68be
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07615550B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes