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Sodium hydride → 1-n-Butyl-3-(beta-diethylaminoethoxy)-4-phenyl-3-pyrrolin-2-one

HRID 1395669
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1395669
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8]N(C)[CH2:6][CH2:5]1.[CH2:11]([N:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([OH:26])[C:16]1=[O:27])[CH2:12][CH2:13][CH3:14].[H-].[Na+].[H][H]>CN(C)C=O>[CH2:11]([N:15]1[CH2:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:17]([O:26][CH2:8][CH2:9][N:4]([CH2:3][CH3:2])[CH2:5][CH3:6])[C:16]1=[O:27])[CH2:12][CH2:13][CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 4137911-(2-Chloroethyl)-4-methylpiperazine2×HCID 205743601-n-Butyl-3-hydroxy-4-phenyl-3-pyrrolin-2-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 205743411-n-Butyl-3-(beta-diethylaminoethoxy)-4-phenyl-3-pyrrolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

N1 -β-chloroethyl-N4 -methylpiperazine, 1-n-butyl-3-[N1 -β-(N4 -methyl)-piperazinoethoxy]-4-phenyl-3-pyrrolin-2-one; dioxalate m.p. 199° C. 32.5 g. (0.14 mol) 1-n-butyl-3-hydroxy-4-phenyl-3-pyrrolin-2-one is added, with stirring, at 40° C. to a suspension of 4.2 g. sodium hydride (80%) in 200 ml. dimethyl formamide. When the evolution of hydrogen ceases, 30.0 g. N1 -β-chloroethyl-N4 -methylpiperazine is added and the mixture allowed to react for 30 minutes at 70° C. The mixture is immediately poured into 1.5 liters of ice water. This is then extracted twice with dichloromethane and the organic phase is washed with water. After drying over anhydrous magnesium sulphate, the solvent is distilled off. The residue (base) is taken up in diethyl ether and oxalic acid is added to precipitate out the di-oxalate. After recrystallization of this dioxalate from aqueous methanol, there is obtained 33.0 g. (44% of theory) of the desired end product.

Aufarbeitung

  1. customto react for 30 minutes at 70° C
  2. extractionThis is then extracted twice with dichloromethane
  3. washthe organic phase is washed with water
  4. dry with materialAfter drying over anhydrous magnesium sulphate
  5. distillationthe solvent is distilled off
  6. additionoxalic acid is added
  7. customto precipitate out the di-oxalate
  8. customAfter recrystallization of this dioxalate from aqueous methanol
  9. customthere is obtained 33.0 g

Quellen und Nachweise

ORD-Eintrag
ord-480428c9b96742b0925cd1233a064f29
Quelldatensatz
uspto-grants-1980_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04205078

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