Hydrochloric Acid → (E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]aniline

HRID 976133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 976133
Cl[C:2]1[C:3]2[CH2:10][CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH:25](O)[CH2:26][C:27]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)=[O:28])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)C([O-])=O.Cl.C(=O)([O-])O.[Na+]>C(O)C>[N:5]1[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=2[C:2]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([C:27](=[O:28])/[CH:26]=[CH:25]/[CH2:24][CH:21]3[CH2:22][CH2:23][N:18]([CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:19][CH2:20]3)=[CH:30][CH:31]=2)=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 133124494-chloro-5H,6H,7H-cyclopenta[d]pyrimidineHCID 867505544-[4-(1-Benzylpiperidin-4-yl)-3-hydroxybutanoyl]aniline.trifluoroacetate

Produkt 1

HCID 19968897(E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]anilineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

30 ml of ethanol and 0.58 g of 4-chloro-5,6-dihydro-7H-cyclopenta[d]pyrimidine were added to 1.21 g of 4-[4-(1-benzylpiperidin-4-yl)-3-hydroxybutanoyl]aniline·trifluoroacetate, 1 ml of an ethanol solution of hydrochloric acid (containing 0.29 g of hydrochloric acid) was added thereto and the mixture was stirred under heating at 60° C. for 40 minutes. Then, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure and the obtained residue was applied to silica gel column chromatography to obtain 0.40 g of the title compound as yellow powder.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-85083f227ce645fd875b7f39a556ff66
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05610303

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