Reacción #2355144

Ecuación de reacción

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

propionaldehyde

indole

sodium hydroxide

→

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

Rendimiento 11.3%

Disolventes

dioxane

acetic acid

dioxane

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   workup.ADDITIONUpon completion of the addition the reaction mixture
3. 3
   OtroThe ether layer was separated
4. 4
   Lavadowashed with water
5. 5
   SecadoThe organic layer was dried with magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   ConcentraciónThe filtrate was concentrated under reduced pressure to an oil, which
8. 8
   LavadoElution
9. 9
   Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente