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1,2-Dimethoxyethane → 1-Methyl-4-(2'-methyl-6-nitro-biphenyl-3-yl)-piperazine

HRID 1043272
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1043272
Br[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C([O-])([O-])=O.[Na+].[Na+].[CH2:24]([CH2:27]OC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:4]2[CH:3]=[C:2]([C:4]3[CH:3]=[CH:2][CH:7]=[CH:6][C:24]=3[CH3:27])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=2)[CH2:12][CH2:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 117815411-(3-Bromo-4-nitrophenyl)-4-methylpiperazine

Produkt 1

HCID 591285961-Methyl-4-(2'-methyl-6-nitro-biphenyl-3-yl)-piperazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 200 mg (0.666 mmol) 1-(3-bromo-4-nitro-phenyl)-4-methyl-piperazine (as prepared in the previous step), 136 mg (0.999 mmol) and 77.0 mg (0.0666 mmol) of tetrakis(triphenylphosphine)palladium (0) under Ar was added 4.0 mL of degassed dimethoxyethane (DME) and 400 μL (0.799 mmol) of 2.0 M aq Na2CO3. The mixture was heated with stirring under Ar at 80° C. for 14 h. The cooled (RT) mixture was concentrated and chromatographed on a 10-g silica SPE column with 1-5% MeOH in dichloromethane-hexane (1:1). The product fractions were treated with 80 mg of decolorizing carbon, filtered, concentrated, and then rechromatographed on a similar column with 1-3% EtOH-dichloromethane to afford 265 mg of the title compound as a yellow resin (75% purity by 1H-NMR as a mixture with triphenylphosphine) that was used in the following reaction without further purification: Mass spectrum (ESI, m/z): Calcd. for C11H21N3O3, 312.2 (M+H). found 312.2.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureThe cooled (RT) mixture
  3. concentrationwas concentrated
  4. customchromatographed on a 10-g silica SPE column with 1-5% MeOH in dichloromethane-hexane (1:1)
  5. additionThe product fractions were treated with 80 mg of decolorizing carbon
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customrechromatographed on a similar column with 1-3% EtOH-dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-66396a997dba46b7b59712e62d8561de
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08557847B2

Notizen zur Reaktion

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