تفاعل #1435678

معادلة التفاعل

sodium sulfide nonahydrate

methyl 2,3-diaminobenzoate

N-acetylpiperidine-4-carbaldehyde

hydrochloricacid

→

product

المردود 75.0%

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

المردود 75.0%

المذيبات

water

water

water

methanol

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   درجة الحرارةthe whole was refluxed for 30 minutes
3. 3
   درجة الحرارةAfter cooling
4. 4
   درجة الحرارةthe 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
   درجة الحرارةAfter cooling
8. 8
   أخرىthe reaction solution was evaporated down under reduced pressure
9. 9
   أخرىThe residue obtained
10. 10
    ترشيحfiltered
11. 11
    استخلاصwas extracted several times with ethyl acetate
12. 12
    غسيلThe combined organic phases were washed with water
13. 13
    أخرىdried
14. 14
    أخرىevaporated down under reduced pressure

الإجراء التجريبي

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.

المصدر