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

HRID 2250노트

반응식

HRID 2250 반응식
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)=[O:15])[C:9](=[O:27])[CH2:8]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[CH2:32](O)[CH3:33]>>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][C:14]([C:16]3[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22]([O:24][CH2:32][CH3:33])=[O:23])=[CH:18][CH:17]=3)=[O:15])[C:9](=[O:27])[CH2:8]2)=[CH:3][CH:2]=1

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 18918395HCID 18918395, 화합물

생성물 1

HCID 18918624Ethyl 4-[2-[4-(4-pyridyl)piperazin-2-one-1-yl]acetyl]phenoxyacetate

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%.

후처리

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. temperatureheated
  3. temperatureat gentle reflux for 21/2 hours
  4. customevaporated
  5. additionThe residue was treated with water
  6. customThe gum which precipitated
  7. customwas separated
  8. extractionextracted with dichloromethane, (2×50 ml)
  9. washThe combined extracts were washed with brine
  10. customdried
  11. customevaporated
  12. customThe residue was purified by chromatography
  13. washMega Bond Elut silica gel column, eluting with 5% methanol/dichloromethane/0.5% triethylamine

출처 및 근거

ORD 기록
ord-b36ff282a19946cb9e1721c4f32fd0ac
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728701

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