تفاعل #1377723

معادلة التفاعل

product

4-[2-[4-(4-Pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetic acid

thionyl chloride

ethanol

→

title product

Ethyl 4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetate

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
2. 2
   درجة الحرارةheated
3. 3
   درجة الحرارةat gentle reflux for 21/2 hours
4. 4
   أخرىevaporated
5. 5
   workup.ADDITIONThe residue was treated with water
6. 6
   أخرىThe gum which precipitated
7. 7
   أخرىwas separated
8. 8
   استخلاصextracted with dichloromethane (2×50 ml)
9. 9
   غسيلThe combined extracts were washed with brine
10. 10
    أخرىdried
11. 11
    أخرىevaporated
12. 12
    أخرىThe residue was purified by chromatography
13. 13
    غسيلMega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine

الإجراء التجريبي

A crude sample of the product of Example 62 (3.4 g) was treated with a solution, at 0° C., made by adding thionyl chloride (2.25 g) dropwise to ethanol (45 ml) with stirring at below 0° C. The mixture was stirred at room temperature for 2 hours, heated at gentle reflux for 21/2 hours, and evaporated. The residue was treated with water and adjusted to pH6 with aqueous sodium bicarbonate solution. The gum which precipitated was separated and the aqueous solution was adjusted to pH8 and extracted with dichloromethane (2×50 ml). The combined extracts were washed with brine, dried and evaporated. The residue was purified by chromatography using a 10 g. Mega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine to give the title product as a solid (0.2 g); m.p. 163°-165° C.; NMR (CDCl3) δ 8.34(2H,m), 6.98(2H,m)(, 6.63(2H,m), 4.89(2H,s), 4.7(2H,s), 4.29(2H,q), 4.1(2H,s), 3.7(2H,m), 3.6(2H,m), 1.31(3H,t); m/e 398(M+H)+ ; calculated for C21H23N3O5 : C, 63.5; M, 5.83; N, 10.6. Found: C, 61.5; H, 5.9; N, 10.5%.

المصدر