Hydrochloric Acid → HCID 21952753, compound

Participants

Reaction Steps

o-Tolylphenylhydrazine hydrogen chloride (25 g, 158.6 mmol) and 4-piperidone monohydrate hydrogen chloride (24.4 g, 158.6 mmol) were suspended in EtOH (310 mL). Concentrated aqueous HCl (26 g, 317 mmol) was then added. The mixture was refluxed for 3 h, and then the reaction was cooled to rt. The ppt was filtered and washed with cold EtOH. The white solid was air-dried for 18 h. 6-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride (36.6 g, 141.2 mmol, 89%) was isolated and a white powder. 1H NMR (CD3OD, 300 MHz) δ 7.22–7.25 (1H, m), 6.89–6.96 (2H, m), 4.40 (2H, m), 3.60 (2H, t, 6.2 Hz), 3.16 (2H, t, 6.2 Hz), 2.45 (3H, s) ppm.

Provenance & Evidence