Cl.[CH3:2][C:3]1([NH2:13])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH3:12])([CH3:11])[CH2:4]1.Br[CH2:15][CH2:16][CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1>[C:18]([CH2:17][CH2:16][CH2:15][NH:13][C:3]1([CH3:2])[CH2:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH3:12])([CH3:11])[CH2:4]1)#[N:19]A mixture of 1,3,3,5,5-pentamethylcyclohexylamine hydrochloride (1) (2-06 g, 10 mmol) 4-bromobutyronitrile (1.55 g. 10.5 mmol) and sodium carbonate (3.18 g, 30 mmol) in tetrahydrofuran (50 ml) was refluxed for 85 h, the poured into water (100 ml) and extracted with ether (3*30 ml). The combined organic phases were washed with brine (20 ml) and dried over K2CO3. The solution was filtered and evaporated and the crude product was purified by chromatography on silica gel, eluting with hexane-ether (10:1), (6:1), (4:1) to give product 2 (1.86 g, 86%) as an colorless oil.
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