Reacción #2355143

Ecuación de reacción

sodium bicarbonate

3-(4-nitrophenyl)-2-propenyl chloride

N-[bis(4-fluorophenyl)methyl]piperazine

N,N-diisopropylethylamine

→

N-[3-(4-nitrophenyl)-2-propenyl]-N′-[bis(4-fluorophenyl)methyl]piperazine

Disolventes

dimethyl sulfoxide

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   TemperaturaAfter this time the reaction mixture was cooled to ambient temperature
3. 3
   workup.STIRRINGwhere it stirred for about 18 hours
4. 4
   Extracciónextracted with three 50 mL portions of diethyl ether
5. 5
   LavadoThe combined extracts were washed with 75 mL of aqueous saturated sodium chloride solution
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   ConcentraciónThe filtrate was concentrated under reduced pressure
9. 9
   Otroyielding a crude oil, which
10. 10
    LavadoElution
11. 11
    Concentraciónconcentrated under reduced pressure

Procedimiento

A solution of 0.5 gram (0.002 mole) of 3-(4-nitrophenyl)-2-propenyl chloride in 5 mL of dimethyl sulfoxide was added to a solution of 0.7 gram (0.002 mole) of N-[bis(4-fluorophenyl)methyl]piperazine in 10 mL of dimethyl sulfoxide. To this was added 0.1 gram (0.0005 mole) of sodium iodide as a catalyst. Upon completion of the addition 1.2 grams (0.010 mole) of N,N-diisopropylethylamine was added dropwise. To effect solution the reaction mixture was then warmed to 50-80° C., where it stirred for four hours . After this time the reaction mixture was cooled to ambient temperature, where it stirred for about 18 hours. The reaction mixture was then poured into 50 mL of aqueous saturated sodium bicarbonate solution and then extracted with three 50 mL portions of diethyl ether. The combined extracts were washed with 75 mL of aqueous saturated sodium chloride solution, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, yielding a crude oil, which was subjected to column chromatography on silica gel. Elution was accomplished with 1:1 ethyl acetate:heptane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.5 gram of of N-[3-(4-nitrophenyl)-2-propenyl]-N′-[bis(4-fluorophenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Fuente