Isopropyl iodide → 1-(1-Methylethyl)-2-piperidinemethanol

In a closed stainless steel tube were heated pyridine-2-methanol (3.27 g, 30 mmol) and 2-iodopropane (3.59 ml, 36 mmol) at 120° C. for 20 hours. A reaction product was dissolved in a methanol-water (10:1) mixture 23 ml) followed by addition of sodium borohydride (1.14 g, 30 mmol). After stirring at room temperature for 3 hours, a reaction solution was concentrated to dryness. To the residue was added water followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product thus obtained was purified by column chromatography on silica gel (SiO2 : 90 g, CHCl3) to give 0.61 g of a product (yield 13%). The substance was then subjected to catalytic hydrogenation (2.7 kg/cm2, 1 hour) at room temperature in ethanol (20 ml) using platinum oxide (0.07 g) as a catalyst. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure to give 0.58 g of the title compound.

1. concentrationa reaction solution was concentrated to dryness
2. additionTo the residue was added water
3. extractionfollowed by extraction with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe crude product thus obtained
7. customwas purified by column chromatography on silica gel (SiO2 : 90 g, CHCl3)

ORD record

ord-a8f269bee9f947e68b262985da576d14

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05124324