Allyl bromide → Diallyl-thiophen-2-ylmethylamine

Participants

Reaction Steps

Allyl bromide (55 ml, 65.4 mmol) is added to a solution of 2-aminomethyl-thiophene (24 ml, 23.3 mmole) and i-Pr2NEt (120 ml, 70.1 mmol) in CH2Cl2 (270 ml). The moderately exothermic reaction spontaneously reaches the reflux temperature after 1 h. The reaction is cooled by means of an ice bath and stirred for 14 h at rt. whereupon an undesired precipitate appeared. This precipitate (45 g) is removed by filtration. The organic layer is evaporated and diluted with EtOAc, whereupon more precipitate appears (45 g), which is removed by filtration. The EtOAc solution is filtered over SiO2 and concentrated to give 36.1 g (80%) of the title diallylamine as a pale yellow oil: 1H NMR (CDCl3) δ 7.25 (br. d, J=5.9 Hz, 1H), 6.98 (br. dd, J=5.1, 2.8 Hz, 1H), 6.94-6.92 (m, 1H), 5.99-5.86 (m, 2H), 5.29-5.18 (m, 4H), 3.85 (s, 2H), 3.16 (dd, J=6.3, 0.9 Hz, 4H).

Provenance & Evidence