Cl[CH2:2][CH2:3][C@@H:4]([N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH2:20][CH3:21])[C:12]1=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[I-].[K+].[CH3:25][NH2:26]>CO>[CH2:20]([N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]([C@@H:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][CH2:2][NH:26][CH3:25])[C:12]1=[O:22])[CH3:21]To a mixture of 1-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one (0.13 g, 0.4 mmol) and potassium iodide (0.2 g, 1.2 mmol) in methanol (5 mL) was added a solution of 33% methylamine in methanol (10 mL). The reaction solution was heated to 80° C. in a sealed tube for 3 hours and cooled to room temperature. The solvent was removed in vacuo and residue purified on a silica gel column (10-50% methanol in methylene chloride) to afford 1-ethyl-3-[(1R)-3-(methylamino)-1-phenylpropyl]-1,3-dihydro-2H-benzimidazol-2-one as an oil. The free base was dissolved in a minimum amount of ethanol and treated with a 2N ethereal solution of hydrochloric acid and stirred for 1 hour. The solvent was removed in vacuo and the residue was triturated with ether/dichloromethane to give 1-ethyl-3-[(1R)-3-(methylamino)-1-phenylpropyl]-1,3-dihydro-2H-benzimidazol-2-one HCl salt as a yellowish amorphous solid (30 mg, 22%). MS (ES) m/z 309.8.
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