Acetone → HCID 23287942, compound

A solution of N-(10-undecenyl)piperidine (3.1 g, 13 mmol), 4-methylmorpholine-N-oxide (1.84 g, 15.7 mmol) and potassium osmate dihydrate (13 mg) in acetone (64 mL) and water (16 mL) were stirred for 6 hours. The reaction was quenched by the addition of 25 mL of a saturated solution of sodium sulphite and stirred for 15 minutes. The reaction mixture was then extracted with ethyl acetate (4×100 mL), the combined organic extract was dried over anhydrous magnesium sulphate and concentrated under reduced pressure. The crude product obtained was further purified by flash chromatography over silica gel using 10% methanol/ethyl acetate eluant to yield 2.5 g (83.4% yield) N-(11,10-dihydroxyundecyl)piperidine (inventive compound no. 1622).

1. customThe reaction was quenched by the addition of 25 mL of a saturated solution of sodium sulphite
2. extractionThe reaction mixture was then extracted with ethyl acetate (4×100 mL)
3. extractionthe combined organic extract
4. dry with materialwas dried over anhydrous magnesium sulphate
5. concentrationconcentrated under reduced pressure
6. customThe crude product obtained
7. customwas further purified by flash chromatography over silica gel using 10% methanol/ethyl acetate eluant

ORD record

ord-bcb5941b931a4602af1caaea4aa05052

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05866576