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Sodium Iodide → N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamine

HRID 1657287
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1657287
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH:10](Cl)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19]([N:21]([CH2:29][CH3:30])[CH2:22][C:23]#[C:24][C:25]([NH2:28])([CH3:27])[CH3:26])[CH3:20].[I-].[Na+]>CC(C)=O>[CH2:29]([N:21]([CH2:19][CH3:20])[CH2:22][C:23]#[C:24][C:25]([NH:28][CH:10]1[CH2:11][C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[CH:9]1)([CH3:26])[CH3:27])[CH3:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 107534844,4-Diphenyl-2-cyclopentenyl chlorideHCID 538468214-Diethylamino-1,1-dimethyl-2-butynylamine

Produkt 1

HCID 19787466N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamineAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180Acetone
Lösungsmittel

Versuchsvorschrift

A mixture of 4,4-diphenyl-2-cyclopentenyl chloride (0.60 g), 4-diethylamino-1,1-dimethyl-2-butynylamine (0.79 g) and a catalytic amount of sodium iodide in acetone (5 ml) was refluxed for 8 hours. After being cooled, the solvent was removed off under reduced pressure and the residue was purified with column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-[4-diethylamino-1,1-dimethyl-2-butynyl]-4,4-diphenyl-2-cyclopentenylamine (0.54 g). The free amine obtained above was dissolved in chloroform, and to the solution was added hydrogen chloride in methanol (0.18 g/ml, 1 ml). The solution was evaporated in vacuo and triturated with a mixture of ethanol and isopropyl alcohol to give its hydrochloride (0.45 g).

Aufarbeitung

  1. temperatureAfter being cooled
  2. customthe solvent was removed off under reduced pressure
  3. customthe residue was purified with column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-9ba77c91ab904f1590191cd4b543f3ac
Quelldatensatz
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05256824

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