[CH3:1][NH:2][C:3]([CH3:15])([CH3:14])[CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br-].[CH:17]1(CO)[CH2:19][CH2:18]1.[C:22](=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>CCC(C)=O>[CH:17]1([CH2:1][N:2]([CH3:22])[C:3]([CH3:15])([CH3:14])[CH2:4][NH:5][C:6](=[O:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:19][CH2:18]1A solution of N-[2-methylamino-2-methyl propyl]benzamide (1 g., 0.0052 mole) in MEK (50 ml.) was added to a solution of cyclopropyl carbinol bromide (0.66 g.,) in MEK (30 ml.) containing sodium carbonate (0.55 g.,) and a few crystals of sodium iodide. The mixture was refluxed for 24 hrs. and then filtered and the excess MEK evaporated under reduced pressure to give a liquid residue. This was passed down an alumina column, eluting with ethyl acetate to give N-[2-[(cyclopropylmethyl)methylamino]-2-methylpropyl]benzamide (0.9 g.).
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