Hexane → HCID 20186855, compound

Participants

Reaction Steps

5-{3-{3-[4-(4-Chlorobenzyl)-1-piperazinyl]-propoxy}phenoxy}-1-(4-methoxybenzyl)-1,2,3-triazole-4-carboxylic acid, (0.50 g, 0.84 mmole), was dissolved in dry dichloromethane (20 ml) and oxalyl chloride, (1.00 ml, 11.7 mmole), added, followed by 1 drop of dimethylformamide. The reaction was stirred overnight, then excess oxalyl chloride and solvent evaporated in vacuo. The acid chloride was resuspended in dry dichloromethane, (20 ml), under nitrogen and cooled with stirring in an ice bath. A 25% solution of ethyl aluminium dichloride in hexane, (1.61 ml, 3.38 mmole) was added dropwise and the reaction stirred in ice for 2 hours, warmed to room temperature over 1 hour, and stirred for a further 3 hours. The mixture was quenched with dilute hydrochloric acid, (50 ml) and left to stand overnight. The resultant cream solid was filtered, stirred in water, (25 ml), and neutralized to pH7 with dilute sodium hydrogen carbonate solution. The aqueous phase was decanted and the gummy residue purified by column chromatography using silica gel, eluting with chloroform to give the title compound as a colourless oil which crystallized on trituration with methanol. 171 mg (35%) mp (MeOH) 135°-138° C. νmax (mull) 1518, 1535, 1565, 1620, 1680 cm-1 δ(CDCl3) 2.00 (2H, m, CH2), 2.50 (10H, bs, piperazinyl+CH2), 3.43 (2H, s, N--CH2), 3.77 (3H, s, OCH3), 4.13 (2H, t, J 6 Hz, OCH2), 5.56 (2H, s, N--CH2), 6.93 (2H, m, aromatics), 7.12 (4H, ABq, Δν 45 Hz, J 9 Hz, C6H4OCH3), 7.29 (4H, s, C6H4Cl) 8.28 (1H, d, J 9 Hz, aromatic).

Provenance & Evidence