Aminoacetaldehyde → (3-Cyclohexyl-propyl)-(2,2-dimethoxy-ethyl)-amine

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Reaction Steps

1-Chloro-3-cyclohexylpropane (11.1 g, 69.0 mmol), 2-aminoacetaldehyde (15.0 mL, 138.0 mmol, 2.0 equiv), and sodium iodide (2.1 g, 14.0 mmol, 0.2 equiv) were combined in anhydrous N,N-dimethylformamide (20 mL). The solution was stirred over solid potassium carbonate (9.66 g, 70 mmol) at 80° C. for 16 hours. The mixture was cooled to room temperature and diluted with water. The solution was extracted with ethyl acetate (2×). The combined organic phase was washed with brine (3×), dried (MgSO4), and concentrated in vacuo to a crude oil. Silica gel chromatography (gradient elution from 50:50 hexane/ethyl acetate to 100% ethyl acetate) yielded the title compound as a yellow oil (12.0 g, 76%). 1H NMR (CDCl3, 300 MHz) δ 4.46 (t, 5.5 Hz, 1H), 3.38 (s, 6H), 2.71 (d, 5.5 Hz, 2H), 2.57 (t, 7.4 Hz, 2H), 1.75-1.60 (m, 3H), 1.47 (m, 2H), 1.17 (m, 8H), 0.86 (m, 2H); Rf=0.27 (50:50 hexane/ethyl acetate).

Provenance & Evidence