Réaction #67958

Équation de réaction

N,N-dimethylformamide

2-(2-bromoethylthio)thiophene

potassium carbonate

1-(trifluoroacetyl)piperidine-4-amine hydrochloride

potassium carbonate

→

N-(2-(2-thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine

Solvants

water

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   Températureunder cooling with ice
3. 3
   Températureunder cooling with ice
4. 4
   workup.STIRRINGthe mixture was stirred for 45 minutes
5. 5
   workup.STIRRINGstirred at 70° C. for 3 hours
6. 6
   TempératureThe reaction mixture was cooled to room temperature
7. 7
   AutreThe organic layer was separated
8. 8
   Lavagewashed with an aqueous saturated sodium chloride solution
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    Autrethe solvent was removed under reduced pressure
11. 11
    AutreThe residue thus obtained
12. 12
    Autrewas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Mode opératoire

To 2 mL of an N,N-dimethylformamide solution containing 0.14 g of 2-(2-bromoethylthio)thiophene, 95 mg of potassium carbonate and 0.16 g of 1-(trifluoroacetyl)piperidine-4-amine hydrochloride were added under cooling with ice, and the mixture was stirred at room temperature for 40 minutes. Thereto was added 95 mg of potassium carbonate under cooling with ice, and the mixture was stirred for 45 minutes, and stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1] to obtain 62 mg of a yellow oily substance, N-(2-(2-thienylthio)ethyl)-1-(trifluoroacetyl)piperidine-4-amine.

Source