Hydrochloric Acid → N-(2-AMinoethyl)acrylaMide hydrochloride

Participants

Reaction Steps

N-t-BOC, N-methyl, N′-acryloyl-ethylenediamine (2.5 mmol, 0.57 g) was stirred in a solution of 3M HCl in ethyl acetate (2.5 cm3) at room temperature for 30 min. The solution was then conc. in vacuo to give the intermediate N-methyl, N′-acryloyl-ethylenediamine monohydrochloride as a clear yellow oil. This intermediate (2.5 mmol) was then stirred at room temperature in 2M NaOH (3 cm3) for 10 min. This reaction mixture was cooled to 0° C., and to this, was added a solution of methacryloyl chloride (2.8 mmol, 0.27 cm3) in chloroform (7 cm3), dropwise, over 30 min. After the addition was complete, the reaction mixture was stirred at 0° C. for a further 1 h. The organic and aqueous phases were then separated, and the aqueous phase extracted with chloroform. The organic extracts were combined, dried (MgSO4), filtered and conc. in vacuo, to give the crude product. The crude product was stirred at room temperature over a slurry of basic alumina in chloroform for 18 hr. Removal of the alumina and concentration of the filtrate then gave a pale yellow oil. Purification by flash chromatography (silica gel, diethyl ether:hexane:methanol elution) afforded N-methyl, N-methacryloyl, N′-acryloyl-ethylenediamine as a pale yellow oil (0.24 g, 48%). δH (300 MHz; CDCl3) 6.79 (1H, br s), NH; 6.2 (1H, d, J 17.1 Hz), HC═CHaHb; 6.08 (1H, dd, J 17.1, 10.0), HC═CHaHb; 5.59 (1H, d, J 10.0 Hz), HC═CHaHb; 5.18 (br m), (H3C)C═CHcHd; 5.00 (br m), (H3C)C═CHcHd; 3.58 (4H, br m), 2×CH2; 3.05, (3H, br m) N(CH3); 1.90 (3H, br m), CH3. δC (75.4 MHz; CDCl3) 170.92, NOC(H3C)C═CH2; 162.87, NHOCHC═CH2; 139.39, (H3C)C═CH2; 132.00, HC═CH2; 125.42, HC═CH2; 119.56, (H3C)C═CH2; 44.97, CH2CH2; 36.21, CH2CH2; 33.98, N(CH3); 19.24, CH3. Found: M+. 196.26.

Provenance & Evidence