1-Iodopropane → HCID 22494700, compound

To a solution of 4-(4-acetylthiopiperidin-1-yl)nitrobenzene (3.34 g) in a mixture of THF (30 ml) and methanol (30 ml) was added 28% sodium methoxide methanol solution (2.67 ml) at 0-5° C. and stirred at the same temperature for 30 minutes. To the mixture was added iodopropane (1.51 ml) at the same temperature and stirred at ambient temperature for 2 hours. The reaction mixture was evaporated in vacuo and dissolved in ethyl acetate (100 ml). The solution was washed three times with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. A solution of the resulting residue, ammonium chloride (1.0 g) and iron powder (4.0 g) in a mixture of ethanol (60 ml) and water (30 ml) was refluxed for 2 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (300 ml) eluting with ethyl acetate. The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-(4-propylthiopiperidin-1-yl)aniline (2.47 g).

1. stirringstirred at ambient temperature for 2 hours
2. customThe reaction mixture was evaporated in vacuo
3. dissolutiondissolved in ethyl acetate (100 ml)
4. washThe solution was washed three times with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. customevaporated in vacuo
7. additionA solution of the resulting residue, ammonium chloride (1.0 g) and iron powder (4.0 g) in a mixture of ethanol (60 ml) and water (30 ml)
8. temperaturewas refluxed for 2 hours
9. customThe reaction mixture was evaporated in vacuo
10. customThe resulting residue was chromatographed on silica gel (300 ml)
11. washeluting with ethyl acetate
12. additionThe fractions containing the desired compound
13. customwere collected
14. customevaporated under reduced pressure

ORD record

ord-7fb24c90683a4fa39a1b04eb8d3fb660

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884868B1