Potassium Carbonate → 4-azido-N-[2-(4-methylpiperazin-1-yl)ethyl]benzamide

Temperatur

75 °C

4-Azido-N-(2-bromoethyl)benzamide (2.0 g) obtained in Example 63a) and potassium carbonate (1.34 g, 9.70 mmol, 1.0 eq.) were suspended in acetonitrile (40 ml), N-methylpiperazine (1.63 ml, 14.6 mmol, 1.5 eq.) was added, and the mixture was stirred at room temperature for 16 hr and at 75° C. for 7 hr. The reaction mixture was concentrated, diluted with water (40 ml) and washed with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted twice with water (20 ml). The aqueous layers were combined, concentrated, saturated with sodium chloride and extracted with ethyl acetate (40 ml and 30 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated at 30° C. or below to give the title compound as a pale-yellow solid (0.69 g, 2.39 mmol, 24.7%).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with water (40 ml)
3. washwashed with ethyl acetate-hexane (2:1, 50 ml)
4. extractionThe organic layer was extracted twice with water (20 ml)
5. concentrationconcentrated, saturated with sodium chloride
6. extractionextracted with ethyl acetate (40 ml and 30 ml)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated at 30° C. or below

ORD-Eintrag

ord-f1407eb0a6154940b8bc473978689490

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07803822B2