Reaktion #499773

Reaktionsgleichung

Hydrogen sulfide

4-(8-chloro-2-cyanonaphthalen-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester

pyridine

→

title compound

4-(2-Amidino-8-chloronaphthalen-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic Acid Ethyl Ester Dihydrochloride

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   SonstigeAfter completion of the reaction
3. 3
   Sonstigethe solvent was evaporated
4. 4
   workup.ADDITIONthe residue was treated with hydrogen chloride-ethanol
5. 5
   workup.ADDITIONTo the residue were added acetone (2 ml), methanol (2 ml) and methyl iodide (0.172 ml)
6. 6
   workup.STIRRINGthe mixture was stirred
7. 7
   Temperaturunder reflux for 2 hours
8. 8
   SonstigeAfter completion of the reaction
9. 9
   Sonstigethe solvent was evaporated
10. 10
    workup.DISSOLUTIONthe obtained residue was dissolved in ethanol (4 ml)
11. 11
    workup.ADDITIONAmmonium acetate (106 mg) was added
12. 12
    workup.STIRRINGthe mixture was stirred at 75° C. for 2 hours
13. 13
    SonstigeAfter completion of the reaction
14. 14
    Sonstigethe solvent was evaporated
15. 15
    Sonstigethe obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia)
16. 16
    workup.ADDITIONThe obtained residue was treated with hydrogen chloride-ethanol
17. 17
    Sonstigedried under reduced pressure

Vorschrift

Hydrogen sulfide was blown into a solution of 4-(8-chloro-2-cyanonaphthalen-7-yloxymethyl)-1-(pyridin-4-yl)piperidine-4-carboxylic acid ethyl ester (124 mg) in a mixture of pyridine (2.5 ml) and triethylamine (0.5 ml) with ice-cooling, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and the residue was treated with hydrogen chloride-ethanol. To the residue were added acetone (2 ml), methanol (2 ml) and methyl iodide (0.172 ml), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was dissolved in ethanol (4 ml). Ammonium acetate (106 mg) was added, and the mixture was stirred at 75° C. for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol:ammonia). The obtained residue was treated with hydrogen chloride-ethanol and dried under reduced pressure to give the title compound (92 mg).

Quelle