Hydrogen Bromide → HCID 68593816, compound

Participants

Reaction Steps

A solution of 2-(8-chloro-2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)ethanol (0.2 g, 0.75 mmol) in aqueous HBr (2 mL) was heated at 120° C. for 15 h. The reaction was monitored by TLC and LCMS. The reaction mixture was basified with solid sodium bicarbonate, extracted with ethyl acetate. Organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain crude product which was purified by silica gel (100-200 mesh) chromatography followed by preparative TLC to obtain 5 mg of 5-(2-bromoethyl)-8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as a free base. The free base (0.005 g 0.0152 mmol) was further dissolved in 2 mL of THF, oxalic acid (0.001 g, 0.015 mmol) in THF (1 mL) was added to it and the resulting mixture was stirred for 30 min at room temperature. The precipitate obtained was filtered and dried under vacuum to afford 1.5 mg of 5-(2-bromoethyl)-8-chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole as oxalate salt. 1H NMR (CD3OD) 7.55 (s, 1H), 7.5 (d, 1H), 7.2 (d, 1H), 4.6 (t, 2H), 4.5 (s, 2H), 3.8 (t, 2H), 3.7-3.6 (m, 2H), 3.3 (bs, 2H), 3.1 (s, 3H).

Provenance & Evidence