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. Author manuscript; available in PMC: 2022 Jul 23.
Published in final edited form as: J Med Chem. 2021 May 20;64(11):7778–7808. doi: 10.1021/acs.jmedchem.1c00611

Scheme 9.

Scheme 9.

a) titanium tetrachloride (TiCl4), triethylamine (TEA), DCM, 0 to 25 ° C, overnight, 58%; b) 4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butan-1-amine, cat. AcOH, STAB, DCE, 25 °C, 4 hrs, 88%; c) H2 (50 psi), Pd/C (20% wet support), EtOH, 25 ° C, 12 hrs; d) HBr 33% in AcOH; 118 ° C, 48 hrs, 13 – 31%; e) 1-(2-chloro-3-ethylphenyl)piperazine14, cat. AcOH, STAB, DCE, 25 ° C, 4 hrs, 88%; f) H2 (30 psi), Pd/C (20% wt.), EtOAc:EtOH (2:1), 25 ° C, 3 hrs, 75%.