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1-Methylpiperazine → 1-(4-Methoxy-3-nitrophenyl)-4-methylpiperazine

HRID 1907438
Notes
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Reaction equation

HRID 1907438 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([N+:46]([O-:48])=[O:47])[CH:39]=1.[CH3:49][N:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([N:53]2[CH2:54][CH2:55][N:50]([CH3:49])[CH2:51][CH2:52]2)=[CH:39][C:40]=1[N+:46]([O-:48])=[O:47]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 62657Potassium Phosphate, TribasicHCID 1185334-Bromo-2-nitroanisoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Product 1

HCID 594418861-(4-Methoxy-3-nitrophenyl)-4-methylpiperazineYield 55%

Reagents, catalysts & solvents 2

HCID 167845
palladium(II) acetate
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

Pd(OAc)2 (85 mg, 0.38 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)-biphenyl (225 mg, 0.57 mmol), K3PO4 (2.26 g, 10.68 mmol), 4-bromo-1-methoxy-2-nitro-benzene (1.77 g, 7.63 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. N-methylpiperazine (1.01 mL, 9.15 mmol) was added and the reaction mixture was refluxed for 72 h. The reaction mixture was then allowed to cool to room temperature and concentrated. The crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 1.05 g (55% yield) of the title compound.

Workup

  1. customflushed with argon
  2. customThe flask was evacuated
  3. temperaturethe reaction mixture was refluxed for 72 h
  4. concentrationconcentrated
  5. customThe crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10)

Sources & evidence

ORD record
ord-26de9f8e385648ebbc55c5d5f1e7a8cd
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598172B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes