[NH:1]1[CH:5]=[N:4][C:3]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)=[N:2]1.[OH-].[Na+].[Br-:21].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.Cl>ClCCl>[Br:21][C:5]1[NH:1][N:2]=[C:3]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[N:4]=1
To a stirred solution of tert-butyl 4-(1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (22 g, 87.19 mmol) in dichloromethane (250 mL) was added sodium hydroxide 2N (131 mL, 261.58 mmol). The reaction mixture was vigorously stirred with mechanical stirring and a solution of benzyltrimethylammonium tribromide (37.4 g, 95.91 mmol) in dichloromethane (250 mL) was then added dropwise, keeping temperature around 15° C. The reaction mixture was left to stir at room temperature for 1 h and 2N HCl was added to give a pH of 5 (keeping temperature around 15° C.). The phases were decanted and the organic phase was washed with H2O (2×1 L), dried over MgSO4, filtered and concentrated to afford tert-butyl 4-(5-bromo-1H-1,2,4-triazol-3-yl)piperidine-1-carboxylate (25.00 g, 87%) as an off-white solid: 1H NMR Spectrum; (CDCl3) 1.46 (9H, s), 1.67-1.84 (2H, m), 1.90-2.13 (2H, m), 2.77-2.96 (2H, m), 2.98-3.10 (1H, m), 3.94-4.35 (2H, m); Mass Spectrum [M+H]+=no mass ion.
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