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Hydrochloric Acid → 1-[3-(2-Furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine

HRID 1885408
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1885408
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[NH:11][CH:10]([C:12]([OH:14])=O)[CH2:9][S:8]2)[CH:2]=1.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.Cl.CN1CCOCC1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CN(C)C=O>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([C:12]([CH:10]2[CH2:9][S:8][CH:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:11]2)=[O:14])[CH2:25][CH2:24]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 7

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 516892Sodium BicarbonateHCID 14772793
1-[3-(2-Furyl)propyl]piperazine

Produkt 1

HCID 147728051-[3-(2-Furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture solution of 2-(3-pyridyl)thiazolidine-4-carboxylic acid 0.5 g, 1-[3-(2-furyl)propyl]piperazine. 2 hydrochloride 0.54 g and N,N-dimethylformamide 5 ml were added N-methylmorpholine 0.2 g and N,N-dimethylformamide 2 ml under ice-cooling. Further 1-hydroxybenzotriazole 0.4 g was added, then dicyclohexylcarbodiimide 0.46 g added and the mixture was stirred overnight at room temperature. Ethyl acetate 50 ml and water 10 ml were added, the solution basified with sodium hydrogen carbonate, the insoluble matter filtered off and the solution transferred into a separtating funnel. The aqueous layer was extracted with ethyl acetate, the extract combined with the organic layer, washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with a mixture solution of ethyl acetate-methanol (4:1) to give 0.25 g of oily 1-[3-(2-furyl)-propyl]-4-[2-(3-pyridyl)thiazolidine-4-ylcarbonyl]piperazine.

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe insoluble matter filtered off
  3. customthe solution transferred into a separtating funnel
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluted with a mixture solution of ethyl acetate-methanol (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-730f1491885e43ac879e4fc6b9420fe1
Quelldatensatz
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05144035

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