Реакция #577368

Уравнение реакции

1-pyridin-2-ylpiperazine

paraformaldehyde

cyclohexanecarboxylic acid amide

potassium carbonate

→

pure compound

Выход 99.2%

N-{[4-(2-pyridinyl)-1-piperazinyl]methyl}cyclohexanecarboxamide

Выход 99.2%

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 under reduced pressure
5. 5
   ДругоеThe residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate)

Методика

A mixture of 1-pyridin-2-ylpiperazine (16 mg, 0.1 mmol, Aldrich), 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 mL absolute ethyl alcohol was heated to reflux under nitrogen overnight. The mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (10% methanol:ethyl acetate) to give 30 mg (66%) pure compound. 1H NMR (500 MHz, DMSO-d6) δ 1.05-1.40 (m, 5H), 1.59-1.68 (m, 5H), 2.15 (m, 1H), 2.48 (m, 4H), 3.45 (t, J=4 Hz, 4H), 3.95 (d, J=5 Hz, 1H), 6.62 (t, J=6 Hz, 1H), 6.81 (d, J=6 Hz, 1H), 7.53 (t, J=6 Hz, 1H), 8.01 (t, J=5 Hz, 1H), 8.10 (d, J=5 Hz, 1H); MS (ESI/APCI−) m/e 301 (M−H)+.

Источник