1-Isopropylpiperazine → (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

HRID 12448

Reaktionsgleichung

Reaktionsgleichung von HRID 12448
[Cl:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]([OH:10])=O)=[CH:4][N:3]=1.[CH:11]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:13])[CH3:12].[Cl-].ClC1N(C)CC[NH+]1C>C1(C)C=CC=CC=1.CCN(C(C)C)C(C)C.CCOC(C)=O>[Cl:1][C:2]1[N:6]([CH3:7])[C:5]([C:8]([N:17]2[CH2:18][CH2:19][N:14]([CH:11]([CH3:13])[CH3:12])[CH2:15][CH2:16]2)=[O:10])=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 780131-IsopropylpiperazineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 534244292-Chloro-1-methyl-1H-imidazole-5-carboxylic acid

Produkt 1

HCID 59338485(2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

Under nitrogen, 2-chloro-3-methyl-3H-imidazole-4-carboxylic acid (0.161 g, 1.0 mmol) is dissolved in toluene (5 mL, anhydrous) and DIEA (0.26 mL). N-isopropylpiperazine (0.2 M in toluene; 5.5 mL; 1.1 mmol) is added followed by the slow addition of 2-chloro-1,3-dimethylimidazolinium chloride (0.3 M in acetonitrile; 4.0 mL; 1.2 mmol). The reaction mixture is stirred at rt for 2 hr and is then diluted with EtOAc and washed with NaOH (1 N). The aqueous layer is drained and reextracted with EtOAc and the combined organic extracts are extracted twice with HCl (1 N). The combined acidic aqueous extracts are washed with EtOAc then basified with NaOH (2.5 M). The resulting basic aqueous solution is extracted three times with EtOAc and the combined organic extracts are washed with brine, then dried over Na2SO4, filtered and concentrated in vacuo.

Aufarbeitung

  1. washwashed with NaOH (1 N)
  2. extractionthe combined organic extracts are extracted twice with HCl (1 N)
  3. washThe combined acidic aqueous extracts are washed with EtOAc
  4. extractionThe resulting basic aqueous solution is extracted three times with EtOAc
  5. washthe combined organic extracts are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1c2f61fb48db41e3902576a0f542c4cc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728009B1

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