Hydrochloric Acid → HCID 23368056, compound

HRID 1901440Notes

Reaction equation

HRID 1901440 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[N:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[N:11]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[OH:3][CH2:4][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[N:18][C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 23368042HCID 23368042, compound

Product 1

HCID 23368056HCID 23368056, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.84 g (7.0 mmol) of 2-(3-ethoxycarbonylpropoxy)-5,6,7,8-tetrahydroquinoxaline was dissolved in 10 ml of tetrahydrofuran (THF), and the solution was ice-cooled. The resultant solution was dropwise added to a suspension of 319 mg (8.4 mmol) of lithium aluminum hydride in 15 ml of THF under ice cooling, followed by stirring for 2 hours at the same temperature as used in the ice cooling above, to thereby effect a reaction. To the resultant reaction mixture was added 2N HCl to thereby acidify the mixture and form a precipitate. The resultant mixture was subjected to filtration to filter off the precipitate, which was then washed with water. The filtrate was extracted with chloroform twice to obtain an extract. The extract was dried over mirabilite, and the solvent was distilled off in vacuo. The resultant residue was purified by silica gel column chromatography. That is, the residue was charged in a column of 50 g of silica gel (C-200, manufactured and sold by Wako Pure Chemical Industries, Ltd.) and eluted with chloroform-methanol (200:1), to thereby obtain 1.55 g of 2-(4-hydroxybutoxy)-5,6,7,8-tetrahydroquinoxaline (yield: 100%).

Workup

  1. temperaturecooled
  2. customa reaction
  3. customTo the resultant reaction mixture
  4. filtrationThe resultant mixture was subjected to filtration
  5. filtrationto filter off the precipitate, which
  6. washwas then washed with water
  7. extractionThe filtrate was extracted with chloroform twice
  8. customto obtain an extract
  9. dry with materialThe extract was dried over mirabilite
  10. distillationthe solvent was distilled off in vacuo
  11. customThe resultant residue was purified by silica gel column chromatography
  12. additionthe residue was charged in a column of 50 g of silica gel (C-200, manufactured and sold by Wako Pure Chemical Industries, Ltd.)
  13. washeluted with chloroform-methanol (200:1)

Sources & evidence

ORD record
ord-36de3934886e41f48630bf2a22d8c463
Source dataset
uspto-grants-1996_11
Patent number
US05578596

Reaction notes

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