Ethyl Acetate → HCID 19733830, compound

Participants

Reaction Steps

A solution of N-Methyl-4-(1-pyrrolidinyl)-2-butynamine (83.4 mg, 0.548 mmol), TEA (153 μL, 1.098 mmol), HMPA (114 μL, 0.657 mmol), and 2-(bromomethyl)-1,3-dioxolane (68 μL, 0.657 mmol) in DMF (2 mL) was stirred at 50 ° C. for 20 h or until complete by TLC. The mixture was poured into EtOAc (20 mL) then washed with 1N NaOH saturated with NaCl (3×20 mL). The organic layer was dried over Na2SO4, and the EtOAc removed in vacuo to give a crude orange oil (102.8 mg, 79% yield). This oil was vacuum distilled to give N-(2,5-dioxolylmethyl)-N-methyl-4-(1-pyrrolidinyl)-2-butynamine as a clear oil: bp 90° C. (0.2 mm Hg); MS (CI-NH3), m/e 239 (MH+); 1H NMR (CDCl3) δ1.74 (br s, 4 H), 2.33 (s, 3 H), 2.58 (br H), 3.37 (s, 2 H), 3.38 (s, 2 H), 3.79 (m, 2 H), 3.92 (m, 2 H), 4.90 (t, J=4.6 Hz, 1 H).

Provenance & Evidence