Isobutyric Acid → HCID 18469925, compound

Participants

Reaction Steps

A 50 mL flask was charged with R 1-(1,2,3,4-tetrahydronaphthyl)-homopiperazine (1.12 g, 4.85 mmol) and isobutyric acid (12.8 g, 145 mmol). The flask was immersed in a 50° C. oil bath. After heating for 10 minutes, NaBH4 was added in portions over 15 minutes. After heating for 16 hours, the resulting mixture was immersed in an ice water bath and water (20 mL) was added. NaOH pellets were added until the solution was strongly basic. The mixture was then extracted with ethyl acetate (3×125 mL) and the combined extracts were dried over anhydrous MgSO4, filtered and concentrated to give a yellow oil. This crude product was purified by simple distillation under reduced pressure using a short-path distillation apparatus (bp=121-126° C., 120 mtorr) to obtain the title compound as a colorless oil (1.19 g). 1H NMR (CDCl3, 300 MHz) δ 0.89 (d, 6H), 1.58-1.76 (m, 5H), 1.93-2.08 (m, 2H), 2.24 (d, 2H), 2.59-2.77 (m, 10H), 3.86 (m, 1H), 7.02-7.18 (m, 3H). 777 (d, 1H); m/s: M+H+ 287.

Provenance & Evidence