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Styrene → 1,4-Dibenzyl-2-styryl-piperazine

HRID 1350373
Notes
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Reaction equation

HRID 1350373 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH:21]=[CH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=C[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C=CC1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru]Cl.ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH:21]=[CH:22][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7501StyreneHCID 111621581,4-Dibenzyl-2-ethenylpiperazine

Product 1

HCID 694896381,4-Dibenzyl-2-styryl-piperazine

Reagents, catalysts & solvents 2

HCID 60145889Benzylidene-bis(triphenylphosphine)ruthenium dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine 1,4-dibenzyl-2-vinyl-piperazine (200.0 mg, 0.68 mmol), styrene (142.5 mg, 1.37 mmol), bis(tricyclohexylphosphine)benzylidine ruthenium (IV) dichloride (168.8 mg, 0.21 mmol), and dichloromethane (8 mL) and stir at reflux. After 24 hours, the reaction mixture was filtered and reduced to residue. The title compound was observed by LC/MS: mass spectrum (ion spray): m/z=369.1 (M+1); Rf=0.49 (hexanes/ethyl acetate (40:60)).

Workup

  1. temperatureat reflux
  2. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-6dd64ff87cb2483baa8d2719021c995f
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07214673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes