Trifluoroacetic acid → HCID 18630917, compound

Participants

Reaction Steps

A solution of 4-quinolin-2-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.072 g, 0.23 mmol) in methylene chloride (5 mL) was added dropwise to a solution of trifluoroacetic acid at 0° C. under N2. After stirring for 45 minutes. at 0° C., the reaction was concentrated to a yellow oil which was slurried in 5% sodium carbonate (5 mL) and stirred for 30 minutes. at ambient temperature. The mixture was concentrated to a yellow solid; the solid was triturated with chloroform (20 mL) which was dried over sodium sulfate. Concentration yielded 2-(1,2,3,6-tetrahydro-pyridin-4-yl)-quinoline (46 mg, 96%) as a yellow oil which was used without further purification. 1H NMR CDC13 δ 8.06 (d, J=9 Hz, 1H), 8.03 (d, J=9 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.68-7.63 (m, 1H), 7.55 (d, J=9 Hz, 1H), 7.46 (t, J=8 Hz, 1H), 6.75-6.40 (m, 1H), 3.70-3.65 (m, 2H), 3.42-3.29 (m, 1H), 3.20 (t, J=6 Hz, 2H), 2.85-2.78 (m, 2H).

Provenance & Evidence