1,2-Dichloroethane → HCID 178522828, compound

Participants

Reaction Steps

Example 8 was prepared by the following procedure. To a solution of trans-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid (F) (444 mg, 1.72 mmol), EDC (328 mg, 1.72 mmol) and HOAt (234 mg, 1.72 mmol) in anhydrous DMF (4 mL) was added benzylamine (184 mg, 1.72 mmol). The resulting reaction mixture was stirred for 15 h. The reaction mixture was partitioned between saturated aqueous NaHCO3 and EtOAc and the organic layer washed 2× with water, and dried with MgSO4. Concentration gave trans-4-(1H-benzimidazol-2-ylmethyl)-cyclohexanecarboxylic acid benzylamide (400 mg, 67%) as a white solid. 1H NMR (400 MHz, CD3OD) δ7.49 (br s, 2 H), 7.30-7.17 (m, 7 H), 4.34 (s, 2 H), 2.78 (d, 2 H), 2.21 (m, 1 H), 1.84 (m, 5 H), 1.55 (q, 2 H), 1.16 (q, 2 H); mass spectrum m/z 348 [(M+H)+; calcd for C22H26N3O: 348].

Provenance & Evidence