Reacción #56061

Ecuación de reacción

5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril hydrochloride

cyclohexanecarboxylic acid chloride

→

5-(1-cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril

Rendimiento 136.8%

Disolventes

trifluoroacetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile refluxing
2. 2
   ConcentraciónThe reaction mixture was concentrated
3. 3
   workup.ADDITIONdiethyl ether was added to the residue
4. 4
   Otroto crystallize the product
5. 5
   OtroThe crystals thus obtained
6. 6
   Otrowere separated by filtration
7. 7
   Lavadowashed with diethyl ether
8. 8
   ExtracciónThe resulting crystals were extracted successively with a saturated aqueous solution of sodium bicarbonate and chloroform
9. 9
   Lavadothe organic layer was washed with water
10. 10
    Otrodried
11. 11
    Concentraciónconcentrated to dryness
12. 12
    OtroThe resulting residue was crystallized from a mixture of diethyl ether and petroleum benzene

Procedimiento

3.36 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril hydrochloride was dissolved in 20 ml of trifluoroacetic acid, and 8.8 g of cyclohexanecarboxylic acid chloride was added to the solution. The mixture was then heated at a temperature of 85° C. while refluxing. The reaction mixture was concentrated and diethyl ether was added to the residue to crystallize the product. The crystals thus obtained were separated by filtration and washed with diethyl ether. The resulting crystals were extracted successively with a saturated aqueous solution of sodium bicarbonate and chloroform, and the organic layer was washed with water, dried and concentrated to dryness. The resulting residue was crystallized from a mixture of diethyl ether and petroleum benzene to obtain 3.59 g of 5-(1-cyclohexylcarbonyloxy-2-isopropylaminobutyl)-8-cyclohexylcarbonyloxycarbostyril having a melting point of 162° to 163° C. (after recrystallization from chloroform-n-hexane).

Fuente