Sulfuric Acid → 2,3,8-trimethyl-5-(2-(6-methylpyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[2-(6-methyl-pyridin-3-yl)-ethyl]-N-p-tolyl-hydrazine (200 mg, 0.829 mmol) in dioxane (7 mL) was added 1,2-dimethyl-piperidin-4-one (137 mg, 1.078 mmol) in dioxane (3 mL) at RT. To this mixture was added sulfuric acid (0.1 mL) at RT. After complete addition the mixture was stirred at 85° C. for 1 h. The reaction was monitored by TLC. After completion of reaction, the mixture was basified with NaHCO3 solution and extracted with EtOAc (300 mL). The organic layer was dried over sodium sulfate, concentrated under vacuum and purified by HPLC to obtain 28.5 mg of desired compound as the TFA salt. 1HNMR (CD3OD, TFA salt) d (ppm): 8.20 (s, 1H), 8.05 (d, 1H), 7.63 (d, 1H), 7.25 (s, 1H), 7.10 (d, 1H), 6.95 (d, 1H), 4.70 (m, 1H), 4.45 (t, 2H), 4.36 (m, 1H), 4.05 (m, 1H), 3.75 (m, 1H), 3.20 (m, 2H), 3.0 (m, 3H), 2.90 (m, 1H), 2.62 (s, 3H), 2.40 (s, 3H), 1.50 (d, 3H).

Provenance & Evidence