Benzyl Bromide → HCID 21462993, compound

Participants

Reaction Steps

A solution of 4-(2-[tetrahydrofuran-2-yl]ethyl)pyridine (3.0 g, 16.9 mmol) in anhydrous dimethylformamide (5 ml) was treated with benzyl bromide (2.2 ml, 18.6 mmol) and the mixture was stirred at room temperature for one hour. The reaction was diluted with absolute ethanol (100 ml), treated with sodium borohydride (0.8 g, 21.2 mmol) and stirred at reflux for one hour. The solvent was evaporated in vacuo and the residue partitioned between diethyl ether and water. The organic layer was separated, dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed with 3% methanol in dichloromethane as eluant to afford the title compound (3.75 g, 82%) as a colourless oil; δH (DMSO-d6) 1.30-2.08 (8H, m, 4×CH2), 2.45-2.52 (2H, m, tetrahydropyridinyl CH2), 2.52-2.56 (2H, m, CH2), 2.60-2.66 (2H, m, tetrahydropyridinyl CH2), 3.50 (2H, s, PhCH2N), 3.52-3.80 (3H, m, tetrahydrofuranyl CH2 and CH), 5.50-5.55 (1H, m, tetrahydropyridinyl 5-H), and 7.20-7.34 (5H, m, ArH); m/z (CI+, NH3) 272 (M+1)+.

Provenance & Evidence