Diethyl Ether → HCID 19090154, Verbindung

HRID 1463370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463370
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[Mg].[CH3:11][N:12]([CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#N)[CH3:13].CC[O:25]CC>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:18]([C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([CH2:14][N:12]([CH3:13])[CH3:11])[CH:16]=2)=[O:25])[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 4

HCID 3283Diethyl Ether3×HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 46410883-(dimethylaminomethyl)benzonitrileHCID 5462224Magnesium

Produkt 1

HCID 19090154HCID 19090154, Verbindung

Versuchsvorschrift

A solution of 5.50 g of 3-chlorobenzyl bromide in 100 ml of dry ether was added slowly to 0.98 g of magnesium in 150 ml of dry ether under nitrogen. The Grignard reagent was stirred at ambient temperature for one hour and then added to a solution of 2.86 g of 3-[(dimethylamino)methyl]benzonitrile in 150 ml of dry ether. The resulting slurry was stirred at room temperature overnight and then quenched with the dropwise addition of saturated ammonium chloride solution. This was diluted with water and the layers separated. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate) and then treated with ethereal HCl until acidic to wet litmus paper. The precipitate was collected and recrystallized from ethanol-ether to give 2.2 g of 2-(3-chlorophenyl)-1-[3-[(dimethylamino)methyl]phenyl]ethanone hydrochloride, m.p. 187°-189° C.

Aufarbeitung

  1. customquenched with the dropwise addition of saturated ammonium chloride solution
  2. additionThis was diluted with water
  3. customthe layers separated
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (silica gel, ethyl acetate)
  9. additiontreated with ethereal HCl until acidic to wet litmus paper
  10. customThe precipitate was collected
  11. customrecrystallized from ethanol-ether

Quellen und Nachweise

ORD-Eintrag
ord-d64bf3cbc0d34f0f9bbb2cae8b4edc1b
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300527

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