Butyl bromide → 1-Butyl-3-methylpiperidine

Participants

Reaction Steps

The first N-substitution of 3-methylpiperidine was carried out using butyl bromide as an N-alkylating agent to form 1-butyl-3-methylpiperidine. An equimolar amount of butyl bromide was added dropwise to a solution of 3-methylpiperidine in methanol keeping the temperature at 20° C. by an ice-water bath. The mixture was hydrolyzed with potassium carbonate, extracted with ether, and dried over Na2SO4. The solution was fractionally distilled at reduced pressure and the fraction with bp 195° C. was collected. 1H-NMR (300 MHz, CDCl3) δ 0.82 (d, 3H), 0.90 (t, 3H), 1.30 (m, 2H), 1.48 (m, 2H), 1.65 (m, 5H), 2.24 (m, 2H), 2.82 (m, 4H).

Provenance & Evidence