Diethyl Ether → HCID 19090154, compound

HRID 1645920Notes

Reaction equation

HRID 1645920 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 19090154HCID 19090154, compound

Procedure

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 etheral 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.

Workup

  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 etheral HCl until acidic to wet litmus paper
  10. customThe precipitate was collected
  11. customrecrystallized from ethanol-ether

Sources & evidence

ORD record
ord-4aa1a251106649ef8136bec16e06a50c
Source dataset
uspto-grants-1993_01
Patent number
US05177111

Reaction notes

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