Sodium Carbonate → 1-(3-Aminophenyl)2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethanol

HRID 15773

Reaktionsgleichung

Reaktionsgleichung von HRID 15773
C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=1)=[O:10].[CH3:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[N:22]=1.[BH4-].[Na+]>O1CCCC1.CO>[NH2:17][C:13]1[CH:12]=[C:11]([CH:9]([OH:10])[CH2:8][N:34]2[CH2:35][CH2:36][N:31]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:28]=3[CH:29]=[CH:30][C:21]([CH3:20])=[N:22]4)[CH2:32][CH2:33]2)[CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 4311764Sodium borohydrideHCID 498519012-Methyl-5-piperazin-1-yl-quinoline

Produkt 1

HCID 574442811-(3-Aminophenyl)2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethanolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium carbonate (1.5 eq) and 2-bromo-1-(3-nitrophenyl)ethanone (1.5 eq) were added to a stirred solution of 2-methyl-5-(1-piperazinyl)quinoline (D3) (1 eq) in tetrahydrofuran at room temperature under an inert atmosphere, and the reaction was left under stirring for 1 h. The solution was then diluted with MeOH, NaBH4 (2 eq) was added and the reaction was left under stirring for 1 h. The solvent was removed under reduced pressure. The crude material was purified on SPE cartridge (SCX) using as eluant a gradient from MeOH to MeOH:CH2Cl2 (1:1) and then 2M NH3 in MeOH affording an intermediate which was reduced following a similar procedure to D6 to give the title compound in 55% yield.

Aufarbeitung

  1. waitthe reaction was left
  2. additionwas added
  3. waitthe reaction was left
  4. stirringunder stirring for 1 h
  5. customThe solvent was removed under reduced pressure
  6. customThe crude material was purified on SPE cartridge (SCX)

Quellen und Nachweise

ORD-Eintrag
ord-59b1fdf8d14e4ce3af11003141c21abf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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