Reaktion #81524

Reaktionsgleichung

[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl chloride

N-[2-[4-(Hydroxymethyl)-1-piperidinyl]ethyl]methanesulphonamide

sodium bicarbonate

→

title compound

[1-[2-[(Methylsulphonyl)amino]ethyl]-4-piperidinyl]methyl[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamate

Lösungsmittel

toluene ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with an air stirrer
2. 2
   workup.ADDITIONthe solids intimately mixed under nitrogen for 10 min at room temperature
3. 3
   Temperaturto cool
4. 4
   workup.STIRRINGThe mixture was vigorously stirred
5. 5
   Sonstigethe layers were separated
6. 6
   Extraktionthe aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml)
7. 7
   Sonstigedried
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto give a beige solid
10. 10
    SonstigeThis was purified by FCC
11. 11
    Wascheneluting with System A (100:8:1)

Vorschrift

[2-(3-Methyl-1,2,4-oxadiazol-5-yl)phenyl]carbamoyl chloride (7.5 g) was placed in a flask equipped with an air stirrer and ground to a powder N-[2-[4-(Hydroxymethyl)-1-piperidinyl]ethyl]methanesulphonamide (9.33 g) was added and the solids intimately mixed under nitrogen for 10 min at room temperature. The mixture was stirred under a stream of nitrogen at 150° for 10 min. The mixture was allowed to cool then toluene/ethanol (10:1; 110 ml) was cautiously added followed by 8% sodium bicarbonate solution. The mixture was vigorously stirred, the layers were separated and the aqueous phase extracted with 10% ethanol in dichloromethane (4×100 ml). The organic solutions were combined and dried and concentrated in vacuo to give a beige solid. This was purified by FCC eluting with System A (100:8:1) to give the title compound (11.83 g) as fluffy off-white needles.

Quelle