N#CBr.[C:4](=[O:7])([O-])[O-].[Na+].[Na+].NCCN1CCC(NC2[N:24]([CH2:25][C:26]3C=CC(F)=[CH:28][CH:27]=3)[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]=2)CC1>O1CCCC1>[O:7]1[CH:4]=[CH:28][CH:27]=[C:26]1[CH2:25][NH:24][C:23]1[C:22]([NH2:21])=[CH:36][CH:35]=[CH:34][CH:33]=1To a stirred mixture of 5.3 parts of cyanogen bromide, 106. parts of anhydrous sodium carbonate and 45 parts of tetrahydrofuran was added dropwise a solution of 18.35 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine in tetrahydrofuran at a temperature between -10° C. and -20° C. Upon completion, stirring was continued for 2 hours at -10° C. After heating to 0° C., the whole was filtered and the filtrate was evaporated, yielding 19 parts (100%) of [2[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]cyanimide as a residue (187).
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