[CH2:1]([N:8]1[CH2:13][CH:12]([CH2:14][OH:15])[CH2:11][CH:10]([CH:16]=[N:17]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].ClC1C=CC=CN1C.CCN(CC)CC.Cl>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH:12]([CH2:14][OH:15])[CH2:11][CH:10]([C:16]#[N:17])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
To 1-benzyl-5-(hydroxymethyl)piperidine-3-carbaldehyde oxime (3.3 g, 13.30 mmol) in CH2Cl2 (15 mL) at 23° C. was added 2-chloro-1-methylpyridine iodide (3.73 g, 14.62 mmol) in one portion and the resulting mixture stirred at 23° C. for 10 min. Et3N was then added and the reaction mixture stirred for 3 hours (color changed from light yellow to light brown). The solution was neutralized with HCl (5%), to approximately pH 6 and the organic material was extracted with CH2Cl2 (3×25 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to afford 3.06 g (95% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.28-7.37 (5 H, m), 3.51-3.60 (4 H, m), 3.11 (1 H, ddd, J=11.0, 1.9, 1.8 Hz), 2.98 (1 H, d, J=7.6 Hz), 2.73-2.82 (1 H, m), 2.12-2.22 (2 H, m), 1.80-1.92 (2 H, m), 1.45 (1 H, br s), 1.27-1.38 (1 H, m). LCMS (+ESI, M+H+) m/z: 231.
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