Reacción #7687

Ecuación de reacción

(S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester

1-pyridin-2-ylpiperazine

potassium phosphate

→

title compounds

Rendimiento 64.2%

(S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester

Rendimiento 64.2%

Disolventes

ethyleneglycol dimethyl ether

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 4 h
2. 2
   Filtraciónthe precipitate was filtered off
3. 3
   ConcentraciónThe filtrate was concentrated under vacuum
4. 4
   OtroThe crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:2)

Procedimiento

A mixture of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5.0 g, 16.7 mmol), 1-pyridin-2-ylpiperazine (10.9 g, 67 mmol), Pd2(dba)3 (1.55 g, 10 mol %), di-t-butyl-biphenylphosphine (0.51 g, 10 mol %), potassium phosphate (7.2 g, 34 mmol) in ethyleneglycol dimethyl ether (40 mL) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL) and the precipitate was filtered off. The filtrate was concentrated under vacuum. The crude product was purified by flash chromatography over silica with ethyl acetate/hexanes (1:2) to provide the title compounds as an oil (4.1 g, 64% yield).

Fuente