Aluminium lithium hydride → HCID 24782240, compound

Participants

Reaction Steps

To a solution of 3-benzyl-4-(1H-indol-5-yl)-piperazine-1-carboxylic acid tert-butyl ester (0.39 g, 1.0 mmol) in 30 mL THF was added LiAlH4 (2.5 mL, 1.0 M in THF). The solution was warmed to reflux for 2 hours, then cooled to room temperature and quenched by the slow addition of 50 mL saturated Rochelle's salt. The mixture was extracted with EtOA, and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Purification via flash chromatography (94:5:1 DCM/MeOH/NH4OH) afforded 5-(2-benzyl-4-methyl-piperazin-1-yl)-1H-indole (0.21 g, 76%); 1H NMR (300, MHz, CDCl3) δ 8.14 (bs, 1H), 7.37 (J=8.7 Hz, 1H), 7.31 (d, J=2.2 Hz, 1H), 7.26-7.05 (m, 1H), 6.52-6.49 (m, 1H), 3.64-3.71 (m, 1H), 3.31-3.21 (m, 1H), 3.20-3.11 (m, 1H), 2.82-2.70 (m, overlapping, 2H), 2.64 (dd, J=13.2, 7.7, 1H), 2.53-2.36 (m, 3H), 2.30 (s, 3H), MS (+H)=306).

Provenance & Evidence