1-Bromo-3-methylbutane → HCID 18469928, compound

Participants

Reaction Steps

A 250 mL flask was charged with a solution of 1-(1,2,3,4-tetrahydronaphthyl)homopiperazine (2.68 g, 11.6 mmol) in THF (105 mL). Triethylamine (2.20 ml, 3.03 g, 29.9 mmol) and 1-bromo-3-methylbutane (2.00 ml, 1.59 g, 10.5 mmol) were added. The solution was immersed in a 60° C. oil bath for 16 hours during which time a precipitate formed. The resulting mixture was filtered and the filtrate was concentrated to give an orange oil. This crude product was purified by column chromatography using diethyl ether:hexane:methanol (5:5:1) to obtain the title compound as a yellow oil (2.34 g). 1H NMR (CDCl3, 300 MHz) δ 0.89 (d, 6H), 1.39 (m, 2H), 1.54-1.79 (m, 5H), 1.92-2.15 (m, 2H), 2.50 (m, 2H), 2.60-2.80 (m, 10H), 3.90 (m, 1H), 7.02-7.18 (m, 3H), 7.77 (d, 2H); m/s: M+H+ 301.

Provenance & Evidence