[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.I[CH2:11][CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:11]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1)[CH2:12][CH3:13]A solution of isonipecotamide (2.0 g, 15.6 mmol), 1-iodopropane (1.52 mL, 15.6 mmol), and potassium carbonate (2.15 g, 15.6 mmol) was heated at reflux in 100 mL of 2-butanone. The solids were filtered and the filtrate concentrated in vacuo to give crude product. Purification by flash chromatography (CH2Cl2—CH3OH, 12:1 ) afforded 1.25 9 of the product as an off-white solid.
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