반응 #438513

반응 방정식

4-chlorophenyl magnesium chloride

8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile

ammonium chloride

→

[-(4-chlorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine

용매

diethylether

diethylether

반응 조건

후처리

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.ADDITIONwere added with ice cooling
3. 3
   기타the phases were separated
4. 4
   세척the ethereal phase was washed in succession with 30 ml water and saturated sodium chloride solution
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated

실험 절차

Starting with 38 ml 1.0 molar 4-chlorophenyl magnesium chloride solution in diethylether, 4.00 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, dissolved in 60 ml diethylether, were added dropwise and stirred overnight at ambient temperature. To work up the mixture, 30 ml ammonium chloride solution (20% by weight) were added with ice cooling, the phases were separated, the ethereal phase was washed in succession with 30 ml water and saturated sodium chloride solution, dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude [-(4-chlorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine (4.18 g) obtained was initially stirred for 24 hours with a mixture of 10 ml concentrated hydrochloric acid (32% by weight) and 6.0 ml water at ambient temperature without further purification and then heated for 3 hours to reflux. Subsequently, the reaction mixture was first washed three times with 50 ml diethylether in each case, then made basic by addition of concentrated ammonia solution (25% by weight) with ice cooling, extracted three times with 100 ml diethylether in each case, the combined diethylether extracts were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. 3.84 g 4-(4-chlorophenyl)-4-dimethylaminocyclohexanone were obtained as a brown oil.

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