Aluminium lithium hydride → 1-[1-(4-Fluorophenyl)cyclopropyl]methanamine

Participants

Reaction Steps

LAH powder (0.153 g, 4.02 mmol) was added portionwise to a solution of 1-(4-fluorophenyl)cyclopropane carboxamide (0.6 g, 3.35 mmol) in THF (10 mL) at rt and the resulting mixture was heated to reflux for 1 h. The suspension was cooled to rt, quenched with MeOH (2 mL), and then 1N HCl (2 mL). The mixture was filtered through Celite, and the Celite washed with 1N HCl (2 mL). The filtrate was made basic with 50% NaOH, and extracted with EtOAc (3×10 mL). The organic extracts were washed with brine, dried over potassium carbonate, and concentrated. The residue was purified by silica gel chromatography using 0-20% 2M ammonia in MeOH/EtOAc as the eluent to give (1-(4-fluorophenyl)cyclopropyl)methanamine (0.5 g, 2.72 mmol, 81% yield) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.35-7.22 (m, 2H), 7.04-6.92 (m, 2H), 2.75 (s, 2H), 1.15 (br. s., 2H), 0.84-0.68 (m, 4H). LCMS: m+1=166.0.

Provenance & Evidence