[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][CH3:11])[C:5]([CH2:6][NH2:7])=[C:4]([CH2:12][CH3:13])[CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][CH3:13])[C:5]([CH2:6][N:7]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH2:10][CH3:11])[CH:9]=14-Bromo-2,6-diethylbenzylamine (90 mg, 0.37 mmol), 1,5-dibromopentane (56 μL, 0.41 mmol) and potassium carbonate (206 mg, 1.5 mmol) were suspended in dioxane (5 mL) and heated at 100° C. overnight. The reaction mixture was then cooled to ambient temperature, the solid removed by filtration and the filtrate concentrated in vacuo to afford an orange oil. The resultant oil was purified by flash chromatography (silica, 12 g column, ISCO, 0-10% methanol in DCM) to afford the title compound as yellow oil (66 mg, 58%). NMR (CDCl3, 300 MHz): 7.16 (s, 2H), 3.38 (s, 2H), 2.80-2.62 (m, 4H), 2.35 (s, 4H), 1.54-1.34 (m, 6H), 1.27-1.13 (m, 6H).
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