2-chloro-6-(4-methylpiperidine-1-carbonyl)pyridine synthesis
- Product Name:2-chloro-6-(4-methylpiperidine-1-carbonyl)pyridine
- CAS Number:912934-67-9
- Molecular formula:C12H15ClN2O
- Molecular Weight:238.71
Yield:912934-67-9 88%
Reaction Conditions:
with dmap;1-hydroxy-7-aza-benzotriazole;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in hexane;dichloromethane;ethyl acetate;N,N-dimethyl-formamide at 20; for 18 h;
Steps:
9
To a solution of 6-chloropyridine-2-carboxylic acid (1.0 g, 6.3 mmol) and 4-methylpiperidine (1.1 mL, 9.5 mmol) in DCM (20 mL) was added EDAC (1.8 g, 9.5 mmol), HOAT (0.5M in DMF, 1.9 mL, 0.95 mmol), and 4-DMAP (116 mg, 0.95 mmol). The solution was stirred at RT for 18 hr, and then was concentrated in vacuo. The residue was partitioned between EtOAc and Brine. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude product was purified via column chromatography (30% EtOAc/70% Hexane, flow rate: 30 mL/min, detection wavelength: 254 nm) to provide compound 9A (1.3 g, 88% yield) as a white solid. HPLC Rt (Method A): 2.91 min. LCMS: m/z 239 (M+H+). HPLC purity: 95%.
References:
US2006/235028,2006,A1 Location in patent:Page/Page column 28