反应 #2346

反应方程式

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

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
2. 2
   温度heated
3. 3
   温度at gentle reflux for 21/2 hours
4. 4
   其他evaporated
5. 5
   workup.ADDITIONThe residue was treated with water
6. 6
   其他The gum which precipitated
7. 7
   其他was separated
8. 8
   萃取extracted with dichloromethane, (2×50 ml)
9. 9
   洗涤The combined extracts were washed with brine
10. 10
    其他dried
11. 11
    其他evaporated
12. 12
    其他The residue was purified by chromatography
13. 13
    洗涤Mega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine

实验过程

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%.

来源