Synthesis and biological evaluation of diamine-based histamine H 3 antagonists with serotonin reuptake inhibitor activity

…, J Wu, TW Lovenberg, NI Carruthers, RL Wolin

Index: Stocking, Emily M.; Miller, Jennifer M.; Barbier, Ann J.; Wilson, Sandy J.; Boggs, Jamin D.; McAllister, Heather M.; Wu, Jiejun; Lovenberg, Timothy W.; Carruthers, Nicholas I.; Wolin, Ronald L. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 11 p. 3130 - 3135

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Citation Number: 13

Abstract

... Reagents ... Scheme 5. Synthesis of H 3 /SERT analogs with an alkyne-linked H 3 component (IV). Reagents and conditions: (a) paraformaldehyde, dimethylamine hydrochloride, concd HCl, 0.6 M EtOH, 90 °C, 24 h (71%); (b) NaBH 4 , EtOH, rt, 16 h (79%); (c) phenol, PS–PPh 3 , DBAD, 0.1 M DCM, rt, 20 h (55%); (d) 1-but-3-ynyl- piperidine, Pd(PPh 3 ) 2 Cl 2 , CuI, HNEt 2 , DMF, 120 °C, 25 min (39%). ...