1-Bromo-3-chloropropane → HCID 23368058, compound

HRID 1901442Notes

Reaction equation

HRID 1901442 reaction equation
[OH:1][C:2]1[CH:11]=[N:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][Cl:22]>C(#N)C>[Cl:22][CH2:21][CH2:20][CH2:19][O:1][C:2]1[CH:11]=[N:10][C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178516734HCID 178516734, compound

Product 1

HCID 23368058HCID 23368058, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 g (10 mmol) of 2-hydroxy-5,6,7,8-tetrahydroquinoxaline was dissolved in 40 ml of acetonitrile. To the resultant solution were added 2.76 g (20 mmol) of potassium carbonate and 1.19 ml (12 mmol) of 1-bromo-3-chloropropane. The resultant mixture was heated under reflux for 2 hours and then, subjected to filtration to thereby filter off insoluble substances. The solvent of the filtrate was distilled off in vacuo to thereby obtain a residue. The obtained residue was purified by silica gel column chromatography. That is, the residue was charged in a column of 42 g of silica gel (Art7734, manufactured and sold by E. Merck, Darmstadt) and eluted with chloroform, to thereby obtain 1.47 g of 2-(3-chloropropoxy)-5,6,7,8-tetrahydroquinoxaline (yield: 67%).

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationsubjected to filtration
  3. filtrationto thereby filter off insoluble substances
  4. distillationThe solvent of the filtrate was distilled off in vacuo
  5. customto thereby obtain a residue
  6. customThe obtained residue was purified by silica gel column chromatography
  7. additionthe residue was charged in a column of 42 g of silica gel (Art7734, manufactured and sold by E. Merck, Darmstadt)
  8. washeluted with chloroform

Sources & evidence

ORD record
ord-06a1f0b55c20484c90ee7cd5de1d82cf
Source dataset
uspto-grants-1996_11
Patent number
US05578596

Reaction notes

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