Реакция #7687

Уравнение реакции

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

1-pyridin-2-ylpiperazine

potassium phosphate

→

title compounds

Выход 64.2%

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

Выход 64.2%

Растворители

ethyleneglycol dimethyl ether

dichloromethane

Условия реакции

Обработка

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

Методика

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).

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