[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.Cl.[CH2:16]([NH:23][CH2:24][CH2:25]Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O.C(Cl)Cl.CO>[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:25][CH2:24][NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1To a chilled suspension of 39.5 g (0.823 mol) 50% sodium hydride in 500 mL dimethylformamide add 37.32 g (0.233 mol) 4-(1H imidazol-1-yl)phenol. When the addition is complete, stir the reaction mixture at room temperature until gas evolution ceases. After this time, chill the reaction mixture below 0° C. and slowly add 60.22 g (0.292 mol) N-benzyl(2-chloro)ethylamine hydrochloride. When the addition is complete, heat the reaction mixture to 65° C. Follow the progress of the reaction by thin-layer chromatography on silica gel (methylene chloride:methanol) (9:1). At the completion of the reaction, add 20 mL water to the cooled mixture. Filter the slats and remove the solvents in vacuo to obtain an oil. Column chromatograph the oil on silica gel using methylene chloride+methanol (1+99→1+19) as eluent. Collect the appropriate fractions and remove the solvents to obtain the title compound as the free base. Dissolve the free base in excess methanolic HCl solution and remove the solvent in vacuo to provide the title compound.
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