Reaktion #7936

Reaktionsgleichung

9a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

cesium carbonate

1-(2-chloroethyl)-piperidine monohydrochloride

→

9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Ausbeute 96.3%

Lösungsmittel

acetone

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Filtrationfiltered
3. 3
   Sonstigeto remove salts
4. 4
   WaschenThe filtrate was washed with water and brine
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated under vacuum to a yellow gum (0.95 g)
8. 8
   SonstigeThe crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 50 mL dry)
9. 9
   Waschenas eluting solvent
10. 10
    workup.ADDITIONThe product containing fractions
11. 11
    Sonstigewere evaporated under vacuum

Vorschrift

A mixture of crude 9a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (787 mg, approx. 2 mmol), cesium carbonate (1.564 g, 4.8 mmol), and 1-(2-chloroethyl)-piperidine monohydrochloride (442 mg, 2.4 mmol) in acetone (5 mL) was stirred and heated in an oil bath at 60° C. for 4 hours. After cooling to room temperature, the mixture was diluted with EtOAc and filtered to remove salts. The filtrate was washed with water and brine, dried over MgSO4, filtered, and evaporated under vacuum to a yellow gum (0.95 g). The crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 50 mL dry) using 2% MeOH+1% Et3N in EtOAc as eluting solvent. The product containing fractions were evaporated under vacuum and the residue stripped with toluene to provide 9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one (912 mg, 96% weight pure) as a pale yellow gum.

Quelle