Potassium Iodide → 2-Chloro-5-[(3-methylpiperidin-1-yl)methyl]pyridine 1-oxide

PS-Diisopropylethylamine (3.54 mmol/g, 0.4 g, 1.40 mmol) was washed with tetrahydrofuran and 2-chloro-5-(chloromethyl)pyridine 1-oxide (100 mg, 0.56 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) was added followed by tetrahydrofuran (1 mL). A solution of 3-methylpiperidine in tetrahydrofuran (1.5 mL) and a catalytic amount of potassium iodide were added, and the mixture was gently stirred (80 r/min) at room temperature for 5 days. PS-Isocyanate (1.10 mmol/g, 1.27 g, 1.40 mmol) was washed with tetrahydrofuran and added to the mixture followed by additional tetrahydrofuran (2 mL). The suspension was gently stirred (80 r/min) at room temperature overnight. N-Ethyl-N,N-diisopropylamine (50 μL, 0.28 mmol) and MP-Carbonate (2.55 mmol/g, 0.66 g, 1.68 mmol) were added, and the containts were mixed and gently stirred for 24 h. The mixture was filtered (20 μm polyethylene filter), and the resins were washed with methylene chloride. Volatiles were removed in vacuo to give 138 mg (99% yield) of the title compound: MS (ES) m/z 241 (M++1).

1. additionwas added
2. additionadded to the mixture
3. stirringThe suspension was gently stirred (80 r/min) at room temperature overnight
4. additionthe containts were mixed
5. stirringgently stirred for 24 h
6. filtrationThe mixture was filtered
7. filtration(20 μm polyethylene filter)
8. washthe resins were washed with methylene chloride
9. customVolatiles were removed in vacuo

ORD record

ord-b4738d6c82a94f6fa9369143a87ec3ae

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399780B2