Reacción #60455

Ecuación de reacción

1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

azetidine hydrochloride

sodium t-butoxide

tri-t-butylphosphonium tetrafluoroborate

→

1-[4-azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine

Disolventes

ethyl acetate

Water

xylene

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe separated organic layer was filtered through Celite
2. 2
   workup.DISTILLATIONThe solvent was distilled off by nitrogen stream to the filtrate
3. 3
   OtroThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

Procedimiento

A mixture of 1-[4-bromo-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine (50 mg, 0.123 mmol) produced in Example (57b), azetidine hydrochloride (17 mg, 0.185 mmol), sodium t-butoxide (47 mg, 0.492 mmol), palladium(II) acetate (3 mg, 0.0123 mmol), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.0369 mmol) and xylene (1 mL) was stirred for 3 hours at an external temperature of 100° C. Water was added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was filtered through Celite. The solvent was distilled off by nitrogen stream to the filtrate. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 1-[4-azetidin-1-yl-2-(4,4-dimethylcyclohexyl)phenyl]-4-butylpiperazine as a colorless solid.

Fuente