Dimethyl Sulfoxide → HCID 86639801, compound

A solution of oxalyl chloride (0.176 mL, 2.015 mmol) in DCM (8 mL) was cooled to −70° C. and treated with anhydrous DMSO (0.238 mL, 3.36 mmol). The resultant solution was stirred at −70° C. for 20 min and then treated with (1-(4-chloro-3-methoxyphenyl)-4-methylpiperidin-4-yl)methanol in DCM (3 mL) and stirred for 40 min. Triethylamine (0.702 mL, 5.04 mmol) was added to the reaction. Upon completion of addition, the mixture was stirred at −70° C. for 30 min and then warmed to RT. The mixture was diluted with DCM, washed with sat NaHCO3, brine, dried (Na2SO4) and concentrated to yield a residue. The residue was purified by flash chromatography on 12 g cartridge to give 1-(4-chloro-3-methoxyphenyl)-4-methylpiperidine-4-carbaldehyde (180 mg, 0.672 mmol, 40% yield) as a pale yellow oil. 1H-NMR (400 MHz, CDCl3) δ ppm 9.50 (1 H, s), 7.18 (1 H, d, J=8.57 Hz), 6.47 (1 H, s), 6.43 (1 H, dd, J=8.57, 1.98 Hz), 3.82-3.89 (3 H, m), 3.27-3.36 (2 H, m), 2.93-3.03 (2 H, m), 2.03-2.12 (2 H, m), 1.57-1.67 (2 H, m), 1.11 (3 H, s).

1. additionUpon completion of addition
2. stirringthe mixture was stirred at −70° C. for 30 min
3. washwashed
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated
6. customto yield a residue
7. customThe residue was purified by flash chromatography on 12 g cartridge

ORD record

ord-7cdd3ebc65cc43c4a9f1716a6d2b3caf

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354432B2