Реакция #577358

Уравнение реакции

1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl hydrochloride

paraformaldehyde

cyclohexanecarboxylic acid amide

potassium carbonate

→

pure compound

Выход 64.0%

N-(3′,6′-dihydro-2,4′-bipyridin-1′(2′H)-ylmethyl)cyclohexanecarboxamide

Выход 64.0%

Растворители

ethyl alcohol

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураto reflux under nitrogen overnight
3. 3
   Фильтрацияfiltered
4. 4
   Другоеthe solvent was removed
5. 5
   ДругоеThe residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

Методика

A mixture of 1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl hydrochloride (20 mg, 0.10 mmol, Saari, W. S.; et al. J. Med. Chem. 1984, 27, 1182), paraformaldehyde (30 mg, 1 mmol), cyclohexanecarboxylic acid amide (64 mg, 0.5 mmol, Aldrich), and 42 mg of potassium carbonate (0.3 mmol) in 2.5 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 19 mg (64%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 1.19 (m, 4H), 1.26 (m, 2H), 1.61 (m, 1H), 1.68 (m, 3H), 2.18 (m, 1H), 2.55 (m, 2H), 2.68 (m, 2H), 3.18 (m, 2H), 4.02 (d, J=5 Hz, 2H), 6.68 (m, 1H), 7.22 (m, 1H), 7.52 (d, J=6 Hz, 1H), 7.73 (t, J=6 Hz, 1H), 8.02 (t, J=5 Hz, 1H), 8.52 (m, 1H); MS (ESI/APCI−) m/e 298 (M−H)+.

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