Cl[C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C@@H:20]1(N)[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]1[NH2:26].[CH:28]1(NCC)CCC[CH2:29]1>O1CCOCC1.[Cu]I>[CH:22]1([CH2:21][N:26]([CH2:28][CH3:29])[C:2]2[C:11]([C:12]#[N:13])=[CH:10][C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=2)[CH2:23][CH2:24][CH2:25][CH2:20]1
Dry dioxane (15 mL) was added to a mixture of 2-chloro-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (3.0 g, 15.62 mmol), potassium carbonate (8.6 g, 62.5 mmol), CuI (5 mol %, 0.064 g), and trans-1,2-cyclohexanediamine (5 mol %, 0.089 g) under an argon atmosphere. A solution of N-cyclopentyl-ethylamine (2.3 g, 18.75 mmol) in dioxane was them added to the stirred reaction mixture, which was then refluxed for 24 h. After this time, the solvent was evaporated under vacuum, and the residue was purified by column chromatography over silica gel (100-200 mesh), eluted with 2% ethyl acetate and petroleum ether, to afford 2-(cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.3 g), yield: 10%.
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