反応 #2346

反応方程式

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

反応条件

後処理

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
   その他evaporated
5. 5
   workup.ADDITIONThe residue was treated with water
6. 6
   その他The gum which precipitated
7. 7
   その他was separated
8. 8
   抽出extracted with dichloromethane, (2×50 ml)
9. 9
   洗浄The combined extracts were washed with brine
10. 10
    その他dried
11. 11
    その他evaporated
12. 12
    その他The residue was purified by chromatography
13. 13
    洗浄Mega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine

実験手順

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%.

出典