Aluminium lithium hydride → HCID 10660028, compound

Participants

Reaction Conditions

Reaction Steps

The obtained 1-(5-fluoro-1H-indol-3-yl)-4-(piperazin-1-yl)butan-1-one dihydrochloride (3.20 g) was dissolved in tetrahydrofuran (50 ml) and cooled to 0° C. A solution of LiAlH4 in tetrahydrofuran (60 ml; 1M, ˜53 mmol LiAlH4) was slowly added. Subsequently, the mixture was heated at 80° C. for 20 hours. The excess LiAlH4 was cautiously hydrolyzed and after extractive work-up, 5-fluoro-3-[4-(piperazin-1-yl)butyl]-1H-indole (2.39 g, 98% yield) was obtained. 1H-NMR (400 MHz, DMSO-d6) δ 1.40-1.50 (m, 2H), 1.61 (quintet, J=7, 2H), 2.12-2.35 (m, 7H), 2.60-2.70 (m, 6H), 6.85-6.92 (m, 1H), 7.17 (d, J˜2, 1H), 7.23 (dd, J˜9 and 2, 1H), 7.30 (dd, J˜9 and 4, 1H), 10.85 (br s, 1H).

Provenance & Evidence