Water → HCID 9974286, compound

Participants

Reaction Steps

In a three-necked flask equipped with a magnetic stirrer and Dean-Stark a solution of 1-methyl-4-piperidone (0.27 ml, 2.4 mmol), 2,4-dimethoxybenzylamine hydrochloride (0.72 gr, 3.5 mmol) and mercaptoacetic acid (0.24 ml, 3.5 mmol) in benzene (5 ml) was refluxed for 3 h. The reaction mixture was cooled to room temperature, water (10 ml) was added and the organic phase was separated. The pH of the aqueous phase was adjusted to pH 10 with 2.5N aqueous sodium hydroxide solution and then the aqueous cooled to room temperature, water (10 ml) was added and the organic phase was separated. The pH of the evaporated. Flash chromatography (silica, 10% methanol in chloroform) of the residue gave AF286 (140 mg, 15% yield). 1H-NMR (CDCl3) δ 1.66 (m, 2H), 2.21 (m, 4H), 2.27 (s, 3H, NCH3), 2.77 (m, 2H), 3.64 (s, 2H, SCH2), 3.78 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 4.52 (s, 2H, NCH2),

Provenance & Evidence