Реакция #53317

Уравнение реакции

water

4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine

4-chloropyridine 1-oxide

sodium hydrogencarbonate

→

title compound

Выход 36.8%

4-[4-(t-butoxycarbonylamino)methyl-4-hydroxypiperidin-1-yl]pyridine 1-oxide

Выход 36.8%

Растворители

isoamyl alcohol

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураunder reflux for 4 hours
3. 3
   Температураto cool
4. 4
   ЭкстракцияThe reaction mixture was extracted with methylene chloride
5. 5
   Промывкаthe organic layer was washed with saturated sodium chloride solution
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   Другоеthe resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1)

Методика

To a suspension in isoamyl alcohol (35 ml) of conventionally known compounds: 4-[(t-butoxycarbonylamino)methyl]-4-hydroxypiperidine (2.00 g) and 4-chloropyridine 1-oxide (1.12 g), was added sodium hydrogencarbonate (1.75 g) and the mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool and water was added thereto. The reaction mixture was extracted with methylene chloride and the organic layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent:methylene chloride:methanol=9:1-4:1) to obtain the title compound (1.03 g).

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