Reacción #7936

Ecuación de reacción

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

Rendimiento 96.3%

Disolventes

acetone

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Filtraciónfiltered
3. 3
   Otroto remove salts
4. 4
   LavadoThe filtrate was washed with water and brine
5. 5
   Secadodried over MgSO4
6. 6
   Filtraciónfiltered
7. 7
   Otroevaporated under vacuum to a yellow gum (0.95 g)
8. 8
   OtroThe crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 50 mL dry)
9. 9
   Lavadoas eluting solvent
10. 10
    workup.ADDITIONThe product containing fractions
11. 11
    Otrowere evaporated under vacuum

Procedimiento

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.

Fuente