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Hydrochloric Acid → 4-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline

HRID 1190865
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1190865
Cl[Sn]Cl.Cl.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]2)[CH2:8][CH2:7]1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[CH2:21][N:22]2[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]2)[CH2:10][CH2:11]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 672468861-Methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine

Produkt 1

HCID 672492344-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]anilineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of SnCl2 (0.398 g, 2.1 mmol), 1.6 mL of HCl 1M and 5 mL of THF was added to a solution of 1-methyl-4-{2-[(4-methylpiperazin-1-yl)methyl]-4-nitrophenyl}piperazine (0.175 g, 2.5 eq) in 15 mL of THF. The reaction mixture was refluxed for 3 h and allowed to cool to room temperature. A saturated aqueous solution of Na2CO3 was added. The aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1) to yield expected compound as a brown oil (100 mg, 63% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (DCM/MeOH/NH4OH//8/2/0.1)

Quellen und Nachweise

ORD-Eintrag
ord-6040fbecdcbf43869eac1b2d1a3fe700
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680095B2

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