C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:23]([CH2:37][CH2:38][CH3:39])[CH:24]([CH2:27][C:28]1[C:36]2[N:35]=[CH:34][NH:33][C:32]=2[CH:31]=[CH:30][CH:29]=1)[CH2:25]O)[CH2:21][CH3:22].C(Br)(Br)(Br)Br>C(Cl)Cl>[CH2:20]([N:23]([CH2:37][CH2:38][CH3:39])[CH:24]1[CH2:27][C:28]2[C:36]3=[C:32]([N:33]=[CH:34][N:35]3[CH2:25]1)[CH:31]=[CH:30][CH:29]=2)[CH2:21][CH3:22]Triphenylphosphine (625 mg, 2.4 mmol) was added to a stirred solution of β-(dipropylamino)-1H-benzimidazole-4-propanol (600 mg, 2.18 mmol) in methylene chloride (12 mL). After solution was complete, carbon tetrabromide (940 mg, 2.8 mmol) was added and the solution was stirred for 30 minutes. Methylene chloride (20 mL) was added and the solution was extracted with 25 mL 1.0 N hydrochloric acid. The methylene chloride was separated, reextracted with 10 mL 1.0 N HCl, and the combined aqueous extracts were basified (20 mL of 4.0 N NaOH) and extracted with ethyl acetate. After removing the ethyl acetate, the product was chromatographed on silica gel using chloroform as the initial eluant to give 380 mg of product. A sample was crystallized from hexane for analysis; mp 95°-98° C. Anal. Calc'd for C16H23N3 : C, 74.66; H, 9.01; N, 16.33. Found: C, 74.28; H, 9.25; N, 16036.
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