Sodium Hydroxide → HCID 49779776, compound

Participants

Reaction Conditions

Reaction Steps

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (145 mg, 0.727 mmol), tetra n-butyl ammonium bromide (11 mg, 0.036 mmol), and 2-methyl-2-(pyridin-4-yl)propyl methanesulfonate (200 mg, 1.20 mmol) were taken into 50% NaOH (6 mL). The reaction mixture was heated overnight at 100° C. Reaction was monitored by TLC and LCMS. After completion of the reaction, the reaction mixture was extracted with EtOAc and water. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude compound was purified by column chromatography to yield 30 mg of product. 1H NMR (CDCl3, Freebase) d (ppm): 8.50 (d, 2H), 7.2-7.13 (m, 3H), 6.88 (d, 2H), 4.03 (s, 2H), 3.62 (s, 2H), 2.63 (t, 2H), 2.50 (s, 3H), 2.42 (s, 3H), 2.25 (t, 2H), 1.43 (s, 6H).

Provenance & Evidence