Reaktion #1756716

Reaktionsgleichung

water

HCl

N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide

borane dimethylsulfide

→

1-(3,4-Dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine

Ausbeute 55.5%

Lösungsmittel

methanol

tetrahydrofurane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was slowly warmed
2. 2
   Temperaturto reflux
3. 3
   Temperaturrefluxed 4 hrs
4. 4
   workup.ADDITIONcautiously added
5. 5
   Temperaturrefluxed for 2 hrs
6. 6
   SonstigeThe crude residue was partitioned between 10% NaOH aqueous solution and ethyl acetate
7. 7
   WaschenThe combined organic phases were washed with water
8. 8
   Trocknendried over sodium sulphate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated to dryness
11. 11
    Sonstigeyielding 94 mg of crude compound which
12. 12
    Sonstigewas purified by column chromatography on silica gel (eluent:petroleum ether/ethyl acetate 50:50 to ethylacetate 100%)

Vorschrift

To an ice cooled solution of N-(1-(3,4-dichlorophenyl)-1H-pyrazol-3-yl)-2-morpholinoacetamide (0.1 g, 0.28 mmol) in dry tetrahydrofurane (4 ml), in a dry nitrogen atmosphere, was dropwise added a 2M solution of borane dimethylsulfide in THF (0.7 ml, 1.4 mmol). The solution was slowly warmed to reflux, refluxed 4 hrs and additionally stirred at room temperature for 16 hrs. The mixture was ice cooled while water (2 ml) and 6M HCl (0.5 ml) cautiously added and, then, refluxed for 2 hrs. Solvents were coevaporated with methanol to dryness in vacuo. The crude residue was partitioned between 10% NaOH aqueous solution and ethyl acetate. The combined organic phases were washed with water, dried over sodium sulphate, filtered and evaporated to dryness yielding 94 mg of crude compound which was purified by column chromatography on silica gel (eluent:petroleum ether/ethyl acetate 50:50 to ethylacetate 100%). 1-(3,4-Dichlorophenyl)-N-(2-morpholinoethyl)-1H-pyrazol-3-amine (53 mg) was obtained as an oil.

Quelle