تفاعل #992770

معادلة التفاعل

3-Ethylpentanoic acid

thionyl chloride

2,6-Dimethyl-4-morpholin-4-yl-phenylamine

sodium bicarbonate brine water

→

title compound

المردود 30.6%

3-Ethyl-pentanoic acid (2,6-dimethyl-4-morpholin-4-yl-phenyl)-amide

المردود 30.6%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   درجة الحرارةheated to 150° C. for 15 minutes in a sealed microwave process vial
3. 3
   استخلاصwas extracted with ethyl acetate (3×50 mL)
4. 4
   تجفيفThe combined organic phases were dried over magnesium sulfate
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe crude product was recrystallized from hot toluene
7. 7
   ترشيحthe product was collected by filtration
8. 8
   غسيلwashed with cold toluene
9. 9
   أخرىdried in vacuo

الإجراء التجريبي

3-Ethylpentanoic acid (0.79 g) and thionyl chloride (0.44 mL) were mixed in acetonitrile (10 mL) and heated to 110° C. for 5 minutes in a sealed microwave process vial. 2,6-Dimethyl-4-morpholin-4-yl-phenylamine (1.25 g) dissolved in acetonitrile (10 mL) was added to the reaction mixture and heated to 150° C. for 15 minutes in a sealed microwave process vial. Saturated aqueous sodium bicarbonate/brine/water (1:1:1, 50 mL) was added to the crude mixture and it was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. The crude product was recrystallized from hot toluene, and the product was collected by filtration, washed with cold toluene and dried in vacuo to furnish 0.59 g (30% yield) of the title compound as an off-white solid. LC-MS (m/z) 319 (MH+); tR=2.04, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, DMSO-d6): 0.87 (t, 6H), 1.35 (qui, 4H), 1.76 (m, 1H), 2.07 (s, 6H), 2.20 (d, 2H), 3.05 (t, 4H), 3.71 (t, 4H), 6.62 (s, 2H), 8.94 (s, 1H).

المصدر