Nitrogen mustard hydrochloride → 3-Bromo-8-(4-methyl-piperazin-1-yl)-quinoline

HRID 883519

Reaktionsgleichung

Reaktionsgleichung von HRID 883519
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].C(=O)([O-])[O-].[Na+].[Na+].[Br:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:27]>C(O)CCC.ClCCl>[Br:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[N:27]1[CH2:8][CH2:7][N:5]([CH3:6])[CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 5935Nitrogen mustard hydrochlorideHCID 10340Sodium CarbonateHCID 151125453-Bromoquinolin-8-amine

Produkt 1

HCID 673136243-Bromo-8-(4-methyl-piperazin-1-yl)-quinolineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

bis-(2-Chloro-ethyl)-methyl-amine hydrochloride (3.7 g, 19.2 mmol) and sodium carbonate (9.0 g, 85 mmol) were added to a suspension of 3-bromo-quinolin-8-ylamine (3.9 g, 17.5 mmol) (for synthesis see Gershon et al., Monatsh. Chem., 1991, 122, 935) in n-butanol (70 ml). The stirred suspension was heated at reflux for 72 h. The reaction mixture was cooled to ambient temperature, diluted with dichloromethane (300 ml) and the solution washed with water (300 ml), dried (MgSO4) and concentrated in vacuo to an oil. The oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane to afford the title compound (D1) as an oil (2.6 g, 8.5 mmol, 49%);

Aufarbeitung

  1. temperatureThe stirred suspension was heated
  2. temperatureat reflux for 72 h
  3. washthe solution washed with water (300 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo to an oil
  6. customThe oil was purified by chromatography over silica gel eluting with a gradient of methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-f8057e4ece724fa39968601bee0eb2f3
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236947B2

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