Reaktion #56061

Reaktionsgleichung

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

cyclohexanecarboxylic acid chloride

→

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

Ausbeute 136.8%

Lösungsmittel

trifluoroacetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile refluxing
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   workup.ADDITIONdiethyl ether was added to the residue
4. 4
   Sonstigeto crystallize the product
5. 5
   SonstigeThe crystals thus obtained
6. 6
   Sonstigewere separated by filtration
7. 7
   Waschenwashed with diethyl ether
8. 8
   ExtraktionThe resulting crystals were extracted successively with a saturated aqueous solution of sodium bicarbonate and chloroform
9. 9
   Waschenthe organic layer was washed with water
10. 10
    Sonstigedried
11. 11
    Einengenconcentrated to dryness
12. 12
    SonstigeThe resulting residue was crystallized from a mixture of diethyl ether and petroleum benzene

Vorschrift

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).

Quelle