반응 #217447

반응 방정식

dodecylamine

nitric acid

ethyl acetoacetate

piperazine

ethyl cyanoacetate

→

Dodecyl Pyridone

수율 85.0%

용매

methanol

water

dimethylformamide

ethanol

반응 조건

후처리

1. 1
   기타Into a 2 liter Erlenmeyer flask equipped
2. 2
   workup.DISTILLATIONto distill away
3. 3
   workup.STIRRINGThereafter, to the hot reaction mixture stirring at 140° C. internal temperature
4. 4
   온도The mixture was then heated to 110° C. for 4 hours
5. 5
   온도to cool to room temperature
6. 6
   기타A white precipitate formed immediately
7. 7
   workup.STIRRINGto stir at room temperature for 3 hours
8. 8
   여과was filtered
9. 9
   세척washed with a 70:30 (v/v) mixture of methanol/deionized water (500 milliliters)
10. 10
    기타oven dried at 60° C.
11. 11
    기타to give 270.5 grams of an off white solid at 85 percent yield

실험 절차

Into a 2 liter Erlenmeyer flask equipped with magnetic stirring was charged dodecylamine (185.0 grams, 1.0 mol; obtained from Sigma-Aldrich) followed with ethyl cyanoacetate (ECA, 135.5 grams, 1.20 mol; obtained from Sigma-Aldrich). The mixture was then heated to 140° C. and stirred at this temperature for 1 hour, during which time the ethanol by-product was allowed to distill away. Thereafter, to the hot reaction mixture stirring at 140° C. internal temperature was sequentially added dimethylformamide (DMF; 250 milliliters), ethyl acetoacetate (EAA; 266.0 grams, 2.0 mol; obtained from Sigma-Aldrich), and piperazine (PIP; 129.0 grams, 1.5 mol; obtained from Sigma-Aldrich). The mixture was then heated to 110° C. for 4 hours. The mixture was then allowed to cool to room temperature and was poured slowly into a mixture of deionized water (1,500 milliliters), methanol (3,500 milliliters), and concentrated nitric acid (270.0 grams, 3.0 mol). A white precipitate formed immediately and was allowed to stir at room temperature for 3 hours, and then was filtered and washed with a 70:30 (v/v) mixture of methanol/deionized water (500 milliliters). The precipitate was then oven dried at 60° C. to give 270.5 grams of an off white solid at 85 percent yield.

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