Synthesis of arylpiperazines via palladium-catalysed aromatic amination reactions of bromoarenes with N-tert-butoxycarbonylpiperazine

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2219-2222

  Kerrigan, Frank ^a   Martin, Claire ^a   Thomas, Gerard H ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; BROMINE DERIVATIVE; PALLADIUM; PIPERAZINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; LIGAND BINDING;

EID: 0032499052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00179-8     Document Type: Article

References (18)

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14. 10. Satisfactory spectral and analytical data were obtained for all new compounds.
15. 14 313-315° C].
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17. 13. Representative procedure : 1,2-Dibromoethane (5.0 ml, 57.6 mmol) was added to a stirred solution of sodium hydroxide (2.5 g) and 2,6-dibromophenol (14.5 g, 57.6 mmol) in water (45 ml). The stirred mixture was heated under reflux for 17 h, cooled and the product extracted into diethyl ether (2 × 100ml). The combined extracts were washed with 1M aqueous sodium hydroxide solution (100 ml) and brine (100 ml), dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography over silica using diethyl ether/petroleum ether (bp 60-80° C) (1:9) as the eluent to give 2-(2,6-dibromophenoxy)ethyl bromide (12.3 g, 61%) as a colourless oil. n-Butyllithium (13.7 ml, 2.5M in hexanes, 34.2 mmol) was added at -80°C under nitrogen to a solution of 2-(2,6-dibromophenoxy)ethyl bromide (12.0 g, 33.5 mmol) in tetrahydrofuran (120 ml) and hexane (30 ml). The mixture was stirred at this temperature for 30 min, allowed to warm to 0° C, and poured into water (100 ml). The layers were separated and the aqueous layer was extracted with diethyl ether (2 × 100 ml). The combined extracts were dried over sodium sulphate and concentrated in vacuo, to give a residue which was purified by flash chromatography over silica using diethyl ether/petroleum ether (bp 60-80° C) (1:24) as the eluent to give 7-bromo-2,3-dihydrobenzo[b]furan (5.8 g, 86%) as a colourless solid, mp 32-34° C.
18. 14. Glennon, R. A.; Slusher, R. M.; Lyon, R. A.; Titeler, M.; McKenney, J. D. J. Med. Chem. 1986, 29, 2377.