Hydrochloric Acid → 2-methyl-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Participants

Reaction Conditions

Reaction Steps

To a suspension of phenylhydrazine (5.4 g) in 75 mL water was added slowly 4.2 mL of 12 N HCl, followed by addition of 1-methylpiperidin-4-one (6.7 g). Additional 16 g of 12N HCl was added and the reaction mixture was heated at 55° C. for 2 days. After cooling in a ice-water bath, 10 N NaOH solution was added slowly until pH>12.20 g of NaCl was added to the mixture and the reaction mixture was extracted with 2×100 mL of CH2Cl2. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was swished from EtOAc to give 7 g of the title compounds as a light yellow solid.

Provenance & Evidence