Benzyl Bromide → HCID 21462998, compound

Participants

Reaction Steps

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethane (2 g, 11.6 mmol) in anhydrous dimethylformamide (5 ml) was treated with benzyl bromide (1.5 ml, 12.7 mmol) and the reaction stirred at room temperature for one hour. The reaction was diluted with ethanol (50 ml), treated with sodium borohydride (0.55 g, 14.5 mmol) and heated at reflux for one hour. The solvent was evaporated and the residue partitioned between ethyl acetate and water. The organic was separated, dried (Na2SO4) and evaporated to give crude product as a yellow oil. This material was triturated with diethyl ether to afford the title compound (2.3 g, 68%) as a colourless solid; δH (DMSO-d6) 1.92-2.10 (2H, m, tetrahydropyridinyl CH2), 2.14-2.30 (2H, m, CH2), 2.36-2.50 (2H, m, CH2), 2.60-2.82 (2H, m, tetrahydropyridinyl CH2), 2.84-2.90 (2H, m, tetrahydropyridinyl CH2), 3.50 (2H, br s, PhCH2N), 5.32-5.44 (1H, m, tetrahydropyridinyl 5-H), 6.02-6.10 (1H, m, furanyl H), 6.30-6.36 (1H, m, furanyl H), 7.16-7.36 (5H, m, ArH), and 7.44-7.52 (1H, m, furanyl H); m/z (CI+, NH3) 268 (M+1)+.

Provenance & Evidence