Hydrochloric Acid → 2,3,4,4a-Tetrahydro-6-Methyl-3-[(4-Pyridinyl)Methyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

HRID 1395455노트

반응식

HRID 1395455 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH2:12][CH2:13][NH:14][CH2:15][CH:4]2[C:3]1=[O:16].Cl.[N:18]1[CH:23]=[CH:22][C:21]([CH2:24]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.CC(C)=O.C(N(CC)CC)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[CH2:12][CH2:13][N:14]([CH2:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)[CH2:15][CH:4]2[C:3]1=[O:16]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 183773372,3,4,4a-tetrahydro-6-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

생성물 1

HCID 203394082,3,4,4a-Tetrahydro-6-Methyl-3-[(4-Pyridinyl)Methyl]-1H-Pyrazino[1,2-a]Quinoxalin-5(6H)-One

시약·촉매·용매 3

HCID 180Acetone용매HCID 702Ethanol용매HCID 8471Triethylamine용매

실험 절차

A solution of 6 g. (0.03 mole) of 2,3,4,4a-tetrahydro-6-methyl-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one, 5 g. (0.03 mole) of 4-picolyl chloride hydrochloride, 10 g. of potassium carbonate and 0.5 ml. of triethylamine was stirred and refluxed in 200 ml. of acetone overnight, cooled and filtered. The solvent was removed and the residue was dissolved in methylene chloride. This solution was washed with water and brine, dried over magnesium sulfate and filtered. The solvent was removed and the residue was chromatographed on 460 g. of Silicar, CC-7. Fractions eluted with 10% methanol in ethyl acetate afforded the product as a free base. This free base was dissolved in ethanol and treated with dry hydrogen chloride saturated ether. The product hydrochloride was filtered and recrystallized from methanol to yield 5.2 g. of the title compound as the dihydrochloride salt, m.p. 252°-254.5° C.

후처리

  1. temperaturerefluxed in 200 ml
  2. filtrationfiltered
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washThis solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed
  9. customthe residue was chromatographed on 460 g
  10. washFractions eluted with 10% methanol in ethyl acetate
  11. customafforded the product as a free base
  12. filtrationThe product hydrochloride was filtered
  13. customrecrystallized from methanol
  14. customto yield 5.2 g

출처 및 근거

ORD 기록
ord-2793b74a74ff41b4886a94d300245c9e
출처 데이터셋
uspto-grants-1980_05
특허 번호
US04203987

반응 노트

불러오는 중…