반응 #2346

반응 방정식

product

4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]-phenoxy acetic acid

thionyl chloride

ethanol

→

title product

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

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
2. 2
   온도heated
3. 3
   온도at gentle reflux for 21/2 hours
4. 4
   기타evaporated
5. 5
   workup.ADDITIONThe residue was treated with water
6. 6
   기타The gum which precipitated
7. 7
   기타was separated
8. 8
   추출extracted with dichloromethane, (2×50 ml)
9. 9
   세척The combined extracts were washed with brine
10. 10
    기타dried
11. 11
    기타evaporated
12. 12
    기타The residue was purified by chromatography
13. 13
    세척Mega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine

실험 절차

A crude sample of the product of Example 36 (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), 7.97(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 C21H23N3 O5 : C, 63.5; M, 5.83; N, 10.6. Found: C, 61.5; H, 5.9; N, 10.5%.

출처