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

HRID 1907438
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HRID 1907438 반응식
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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-26de9f8e385648ebbc55c5d5f1e7a8cd
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598172B2

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