Реакция #1435678

Уравнение реакции

sodium sulfide nonahydrate

methyl 2,3-diaminobenzoate

N-acetylpiperidine-4-carbaldehyde

hydrochloricacid

→

product

Выход 75.0%

Methyl 2-(N-acetylpiperidin-4-yl)benzimidazole-4-carboxylate

Выход 75.0%

Растворители

water

water

water

methanol

methanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   Температураthe whole was refluxed for 30 minutes
3. 3
   ТемператураAfter cooling
4. 4
   Температураthe whole was again refluxed
5. 5
   workup.ADDITIONwere then added dropwise
6. 6
   workup.WAITthe whole was boiled for a further 10 minutes
7. 7
   ТемператураAfter cooling
8. 8
   Другоеthe reaction solution was evaporated down under reduced pressure
9. 9
   ДругоеThe residue obtained
10. 10
    Фильтрацияfiltered
11. 11
    Экстракцияwas extracted several times with ethyl acetate
12. 12
    ПромывкаThe combined organic phases were washed with water
13. 13
    Другоеdried
14. 14
    Другоеevaporated down under reduced pressure

Методика

3.3 g (19.9 mmol) of methyl 2,3-diaminobenzoate were dissolved in 100 ml of methanol, and a solution of 4.0 g (25.8 mmol) of N-acetylpiperidine-4-carbaldehyde in 100 ml of methanol was added dropwise at room temperature. The whole was stirred for about 10 minutes at room temperature. Thereafter, 5.2 g (25.8 mmol) of copper(II) acetate, which was dissolved in 100 ml of water, were added dropwise and the whole was refluxed for 30 minutes. After cooling, 25 ml of concentrated hydrochloricacid were added carefully and the whole was again refluxed. 7.15 g (29.8 mmol) of sodium sulfide nonahydrate, dissolved in 100 ml of water, were then added dropwise and the whole was boiled for a further 10 minutes. After cooling, the reaction solution was evaporated down under reduced pressure. The residue obtained was dispersed in water and filtered. The filtrate was rendered alkaline with aqueous sodium bicarbonate solution and was extracted several times with ethyl acetate. The combined organic phases were washed with water, dried and evaporated down under reduced pressure. 4.5 g of the product were obtained.

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