Sodium Chloride → HCID 78879010, compound

N-Methoxy-N-methylpiperidine-4-carboxamide hydrochloride (600 mg, 2.88 mmol) in water (5 mL) was adjusted to pH 10 with 1 M aqueous sodium hydroxide and extracted with 1-butanol. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a colorless solid. The resulting solid (200 mg, 1.16 mmol) was dissolved in N,N-dimethylformamide (4 mL) and stirred with potassium carbonate (481 mg, 3.48 mmol) and 2,2,2-trifluoroethyl trifluoromethanesulfonate (335 μL, 2.32 mmol) at room temperature for one day. After addition of water and saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol/chloroform=1/19→1/9 (v/v)) to give the title compound as a colorless oil (190 mg, yield 26%).

1. extractionextracted with 1-butanol
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customto give a colorless solid
5. extractionthe reaction mixture was extracted with ethyl acetate
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography (methanol/chloroform=1/19→1/9 (v/v))

ORD record

ord-9c382829747d4f93ab4f9c9fd1a665bc

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2