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N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2,4-triazolo[4,3-a]pyridine-3-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With ammonia; In ethanol; dichloromethane;
(a) N-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]-1,2,4-triazolo-[4,3-a]pyridine-3-amine 3-Bromo-1,2,4-triazolo[4,3-a]pyridine (2.5 g), 3-[3-(1-piperidinylmethyl)phenoxy]propanamine (9 g) and ethanol (20 ml) were heated in an autoclave at 110 for 24 h and then at 150 for 36 h. The mixture was evaporated in vacuo (200, 0.1 mm Hg) and the residue (2.3 g) was chromatographed on silica using dichloromethane:ethanol:880 ammonia (100:8:1) to give a gum which was crystallized from methyl acetate-petroleum ether (b.p. 60-80) to give the title compound (0.8 g) as white crystals, m.p. 150-151. Found: C, 69.0; H, 7.4; N, 19.1; C21 H27 N5 O requires: C, 69.0; H, 7.45; N, 19.2%.
With N-Bromosuccinimide; potassium carbonate; potassium penicillin V; In chloroform;
3-bromo[1,2,4]triazolo[4,3-a]pyridine A mixture of [1,2,4]triazolo[4,3-a]pyridine (1.26 g) and NBS (1.98 g) with chloroform is refluxed for 5 h and then left for 14 h at room temperature. A saturated aqueous solution of potassium carbonate (200 ml) and KOH (20 g) are added, the mixture is shaken and the organic layer is separated. The aqueous layer is extracted with DCM twice. The combined organic extract is dried over Na2SO4 and the solvent is evaporated in vacuum giving the desired product with 60% yield.
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