4-Methylphenylhydrazine monohydrochloride → HCID 66612137, compound

Participants

Reaction Steps

A solution of (4-methylphenyl)hydrazine hydrochloride (1.5 g, 0.00948 mol) and 1-cyclopropylpiperidin-4-one (1.3 g, 0.00948 mol) in 7% sulfuric acid in dioxane (20 mL) was heated at 80° C. for 2 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and the dioxane layer was decanted. The residue was basified with 10% sodium hydroxide solution and extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated affording crude material, which was purified by silica gel column chromatography (2% MeOH:DCM) to yield 2-cyclopropyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.4 g, 66% yield).

Provenance & Evidence