Benzyl Bromide → (1-Benzyl-1,2,3,6-tetrahydropyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 4-hydroxymethylpyridine (20 g, 0.183 mol) in anhydrous dimethylformamide (70 ml) was treated with benzyl bromide (24 ml, 0.202 mol) and the mixture was stirred at 100° C. for two hours. The reaction was cooled to room temperature and diluted with absolute ethanol (250 ml). Sodium borohydride (8.7 g, 0.229 mol) was added portionwise and the mixture stirred at reflux for 3 hours. The solvent was evaporated in vacuo and the residue partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed with 1:1 hexane/ethyl acetate as eluant to the title compound (13 g, 35%) as a lemon yellow solid; δH (CDCl3) 2.12-2.20 (2H, m, tetrahydropyridinyl CH2), 2.60 (2H, t, J 7.5 Hz, tetrahydropyridinyl CH2), 2.96-3.04 (2H, m, tetrahydropyridyl CH2), 3.60 (2H, s, PhCH2N), 4.00-4.04 (2H, m, CH2OH), 5.60-5.66 (1H, m, tetrahydropyridinyl 5-H), and 7.20-7.40 (5H, m, ArH). m/z (CI+, NH3) 204 (M+1)+.

Provenance & Evidence