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Piperazine → 1-(2-Phenoxyphenyl)piperazine

HRID 334260
Notes
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Reaction equation

HRID 334260 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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>[O:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 4837PiperazineHCID 374831-Bromo-2-phenoxy-benzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 129967051-(2-Phenoxyphenyl)piperazineYield 64.3%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-Catalyst
HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1-Bromo-2-phenoxybenzene (432 mg, 1.73 mmol), piperazine (299 mg, 3.47 mmol), Pd2(dba)3 (48 mg, 0.052 mmol), BINAP (54 mg, 0.087 mmol) and NaOt-Bu (249 mg, 2.60 mmol) were dissolved in toluene (10 mL) in a reaction vessel and refluxed at 100° C. for 20 hours. After the reaction was completed, the reaction mixture was diluted with EtOAc and filtered through Celite. The filtrate was concentrated under reduced pressure and the concentrate was purified by column chromatography (MC:mixture solution (MC:MeOH:H2O:NH3=80:20:1:1)=6:1) to obtain 283 mg of the target compound (1.11 mmol, 64.3%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe concentrate was purified by column chromatography (MC:mixture solution (MC:MeOH:H2O:NH3=80:20:1:1)=6:1)

Sources & evidence

ORD record
ord-9054b7bb75124ffa982ebcd6d7142cc6
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883796B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes