Reaction Steps
To a solution of N-cyano-N'-[3-(4-phenyl-1-piperidinyl)propyl]isothiourea sodium salt (IX) (115 mg, 0.35 mmol) and the aniline intermediate (XIV) from Example 12 (115 mg, 0.35 mmol) in THF (7 mL) at 0° C. was added HgCl2 (95 mg, 0.35 mmol). The reaction mixture was then refluxed for 3 h. After cooling to room temperature, H2O (1 mL) was added, and the mixture was stirred for 30 min. A gray precipitate was collected by filtration, and rinsed with CH2Cl2, the organic extract was dried (Na2SO4), and the solvent was removed in vacuo. The residue was subjected twice to flash chromatography (silica gel, MeOH:CH2Cl2, 4:96) to afford the compound as a white solid (15 mg, 4.5%). mp 85-90° C.; MS (ESI) m/z 599 (MH+); 1H NMR (CDCl3) δ 7.30 (m, 8 h), 6.98 (d, 1H, J=7.8 Hz), 6.91 (s, 1H), 5.29 (br s, 1H), 5.09 (s, 1 H), 3.67 (s, 6H), 3.63 (m, 2H), 3.47 (m, 2H), 3.37 (s, 3H), 3.00 (m, 2H), 2.73 (m, 4H), 2.45 (s, 6H), 2.38 (m, 1H), 2.26 (m, 2H), 2.03 (m, 2H); 13C NMR (CDCl3) δ 168.2, 150.4, 146.8, 130.6, 129.0, 128.0, 127.4, 127.0, 124.9, 124.1, 117.3, 102.3, 54.1, 51.4, 51.3, 40.8, 40.3, 39.9, 38.9, 30.4, 25.4, 19.3. HRMS (FAB) Calcd. for C34H43N6O4 (MH+): m/z 599.3346. Found: 599.3362.
