[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6](O)=[O:7].CC[N:18]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][C:5]([CH3:10])([CH3:9])[C:6]([NH2:18])=[O:7]A mixture of 3-((3-endo-amino-8-azabicyclo[3.2.1]octan-8-yl)methyl)benzonitrile dihydrochloride (470 mg, 1.49 mmol), commercially available 2-(2,4-dichlorophenoxy)-2-methylpropanoic acid (4) (447 mg, 1.79 mmol), EDCI (430 mg, 2.24 mmol), HOBT (304 mg, 2.24 mmol) and triethylamine (1.3 mL, 9.32 mmol) in CH2Cl2 (5 mL) was stirred 18 h. The resulting mixture was washed with satd. aq. NaHCO3 solution (5 mL), brine (5 mL) successively, dried over MgSO4, filtered and evaporated to give a residue which was purified by column chromatography (ethyl acetate: CH2Cl2=1:1) to give N-(8-(3-cyanobenzyl)-8-azabicyclo[3.2.1]octan-3-endo-yl)-2-(2,4-dichlorophenoxy)-2-methylpropanamide (526 mg, 1.11 mmol, 74% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 1.55 (s, 6H), 1.65 (d, 2H), 1.85 (m, 2H), 2.08 (m, 2H), 2.25 (m, 2H), 3.15 (br s, 2H), 3.55 (ABq, 2H), 4.17 (m, 1H), 7.04 (d, 1H), 7.20 (dd, 1H), 7.44 (m, 2H), 7.48 (m, 1H), 7.54 (m, 1H), 7.62 (d, 1H), 7.70 (br s, 1H).
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