Potassium Carbonate → 3-Cyclopentyl-propyl (2,2-dimethoxy-ethyl)-amine

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A mixture of 2-aminoacetaldehyde dimethyl acetal (3.0 mL, 27.5 mmol), solid potassium carbonate (2.1 g, 15.2 mmol), and 3-cyclopentyl-1-iodopropane (3.3 g, 13.9 mmol) in anhydrous N,N-dimethylformamide was stirred for 12 hours at room temperature. The mixture was filtered, and the filtrate was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and concentrated to a crude oil. The crude was passed through a plug of silica gel with ethyl acetate to provide a yellow oil (2.67 g, 89%). 1H NMR (300 MHz, DMSO-d6) δ 4.35 (t, 1H), 3.23 (s, 6H), 2.54 (d, 2H), 1.70 (m, 3H), 1.51 (m, 6H), 1.36 (m, 2H), 1.27 (m, 2H), 1.04 (m, 2H).

Provenance & Evidence