반응 #2355144

반응 방정식

N-[(4-chlorophenyl)(phenyl)-methyl]piperazine

propionaldehyde

indole

sodium hydroxide

→

N-[1-(indol-3yl)propyl]-N′-[(4chlorophenyl)-(phenyl)methyl]piperazine

수율 11.3%

용매

dioxane

acetic acid

dioxane

diethyl ether

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   workup.ADDITIONUpon completion of the addition the reaction mixture
3. 3
   기타The ether layer was separated
4. 4
   세척washed with water
5. 5
   건조The organic layer was dried with magnesium sulfate
6. 6
   여과filtered
7. 7
   농축The filtrate was concentrated under reduced pressure to an oil, which
8. 8
   세척Elution
9. 9
   농축concentrated under reduced pressure

실험 절차

A solution of 2.0 grams (0.006 mole) of N-[(4-chlorophenyl)(phenyl)-methyl]piperazine and 0.5 mL (0.007 mole) of propionaldehyde in 8.0 mL of dioxane and 8.0 mL of glacial acetic acid was stirred and cooled in an ice bath. To this a solution of 0.7 gram (0.006 mole) of indole in 10.0 mL of dioxane was added dropwise during a 15 minute period. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours, after which the reaction mixture was poured into a mixture of diethyl ether and aqueous 5% sodium hydroxide. The ether layer was separated and washed with water and then with an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to an oil, which was subjected to column chromatography on silica gel. Elution was accomplished with pure hexane, followed by diethyl ether/hexane mixtures and then pure diethyl ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of N-[1-(indol-3yl)propyl]-N′-[(4chlorophenyl)-(phenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

출처