반응 #2355139

반응 방정식

(2-chlorophenyl)(4-chlorophenyl)methyl chloride

ethyl 1-piperazine-carboxylate

triethylamine

sodium iodide

→

N-(ethoxycarbonyl)-N′-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine

수율 28.3%

용매

toluene

methylene chloride

hexane

methylene chloride

반응 조건

후처리

1. 1
   온도at reflux for about 18 hours
2. 2
   여과The resulting precipitate was collected by filtration
3. 3
   workup.ADDITION200 mL of aqueous saturated sodium bicarbonate solution was added to it
4. 4
   추출The mixture was extracted with two 100 mL portions of ethyl acetate
5. 5
   세척The combined ethyl acetate layers were washed with two 25 mL portions of an aqueous saturated sodium chloride solution
6. 6
   건조The organic layer was dried with sodium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타yielding 3.2 grams of crude material
9. 9
   농축concentrated under reduced pressure

실험 절차

A stirred solution of 2.5 grams (0.009 mole) of (2-chlorophenyl)(4-chlorophenyl)methyl chloride, 1.6 grams (0.010 mole) of ethyl 1-piperazine-carboxylate, 1.4 mL (0.010 mole) of triethylamine, and 1.2 grams (0.008 mole) of sodium iodide in 25 mL of toluene was heated at reflux for about 18 hours. The resulting precipitate was collected by filtration. The filtrate was cooled to ambient temperature and 200 mL of aqueous saturated sodium bicarbonate solution was added to it. The mixture was extracted with two 100 mL portions of ethyl acetate. The combined ethyl acetate layers were washed with two 25 mL portions of an aqueous saturated sodium chloride solution. The organic layer was dried with sodium sulfate and concentrated under reduced pressure, yielding 3.2 grams of crude material. The crude material was subjected to column chromatography on silica gel with 50-25% hexane in methylene chloride, followed by pure methylene chloride, as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.0 gram of N-(ethoxycarbonyl)-N′-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

출처