Reaktion #2505014

Reaktionsgleichung

5-cyanopentyl-imidazo[1,5-a]pyridine

sodium azide

lithium chloride

ammonium chloride

→

5-[5-(5-tetrazolyl)pentyl]imidazo[1,5-a]pyridine

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationfiltering
3. 3
   Sonstigethe solvent is evaporated
4. 4
   workup.DISSOLUTIONthe residue is dissolved in 50 ml of water
5. 5
   Extraktionextracted with 25 ml of ethyl acetate
6. 6
   FiltrationThe precipitated solid is filtered
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried

Vorschrift

A solution of 5-(5-cyanopentyl-imidazo[1,5-a]pyridine (5.26 g) in 16 ml of dry dimethylformamide is heated at 120° for 15 hours with sodium azide (2.15 g), lithium chloride (0.2 g) and ammonium chloride (1.80 g). After cooling and filtering, the solvent is evaporated and the residue is dissolved in 50 ml of water, extracted with 25 ml of ethyl acetate and brought to pH=5 with concentrated sulfuric acid. The precipitated solid is filtered, washed with water and dried to yield 5-[5-(5-tetrazolyl)pentyl]imidazo[1,5-a]pyridine, m.p. 149°-150°. The mono-hydrochloride salt has m.p. 188°-190°.

Quelle