Diethyl Ether → HCID 19090154、化合物
反応式
[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]=1参加物
実験手順
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.
後処理
- customquenched with the dropwise addition of saturated ammonium chloride solution
- additionThis was diluted with water
- customthe layers separated
- extractionThe aqueous phase was extracted with ethyl acetate
- dry with materialthe combined organic extracts were dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe residue was purified by flash chromatography (silica gel; ethyl acetate)
- additiontreated with ethereal HCl until acidic to wet litmus paper
- customThe precipitate was collected
- customrecrystallized from ethanol-ether
出典と根拠
- ORDレコード
- ord-05f87aa22eb64e4d81504035a115feaf
- 出典データセット
- uspto-grants-1991_04
- 特許番号
- US05006563
反応ノート
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