Benzylamine → Benzyl-[4-(4-methylpiperazine-1-sulfonyl)-2-nitrophenyl]amine

HRID 1012120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012120
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 28424191-[(4-Chloro-3-nitrophenyl)sulfonyl]-4-methylpiperazine

Produkt 1

HCID 9186770Benzyl-[4-(4-methylpiperazine-1-sulfonyl)-2-nitrophenyl]amineAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(4-Chloro-3-nitro-benzenesulphonyl)-4-methyl-piperazine (0.50 g, 1.57 mmol) and benzylamine (0.502 g, 4.70 mmol) were dissolved in THF (10 ml) and heated at reflux for 3 h. The reaction mixture was then reduced in vacuo and partitioned between ethyl acetate and water. The organics were washed with brine, dried (MgSO4) and reduced in vacuo, and the resultant residue purified by column chromatography eluting with 0-10% methanol in ethyl acetate to give benzyl-[4-(4-methyl-piperazine-1-sulphonyl)-2-nitro-phenyl]-amine as a yellow solid (0.53 g, 86%). (LC/MS: Rt 2.21, [M+H]+ 391.05).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. custompartitioned between ethyl acetate and water
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe resultant residue purified by column chromatography
  7. washeluting with 0-10% methanol in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-761432d5449f4fc5bcfd9424fcf7b744
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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