Water → HCID 9882968, compound

Participants

Reaction Steps

Lithium aluminium hydride in THF (1M, 11.25 mmol) was slowly added to a suspension of 2-(4-benzylpiperazin-1-yl)carbonyl indole hydrochloride (2.0 g, 5.6 mmol) in THF (40 ml) under a nitrogen atmosphere and the resultant solution heated at reflux for 90 min. The mixture was cooled to room temperature and treated sequentially with water (0.5 ml), sodium hydroxide (4M, 0.5 ml) and water (1.5 ml). The mixture was filtered and the filtrate evaporated in vacuo. The residue was recrystallised from toluene to afford the title compound as a white solid (428 mg, 25%), m.p. 157°-159° C.; (Found: C, 78.44; H, 7.63; N, 13.66. C20 H23N3 requires C, 78.65; H, 7.59; N, 13.76%); δH (DMSO-d6) 2.40 (8H, br s, 4×piperazinyl CH2), 3.45 (2H, s, CH2), 3.59 (2H, s, CH2), 6.23 (1H, s, 3-H), 6.90 (1H, m, ArH), 6.95 (1H, m, ArH), 7.20-7.32 (6H, m, ArH), 7.42 (1H, d, J 7.7 Hz, ArH), and 10.93 (1H, br s, NH); m/z (CI+, NH3) 306 (M+1)+.

Provenance & Evidence