1,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline → 7-Bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline

HRID 1765412Notes

Reaction equation

HRID 1765412 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH3:14])=[CH:11][CH:12]=2)[N:7]([CH:15]([CH3:17])[CH3:16])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[Br-:18].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[Br:18][C:11]1[CH:12]=[C:13]2[C:8]([N:7]([CH:15]([CH3:17])[CH3:16])[CH2:6][CH2:5][N:4]2[CH:1]([CH3:3])[CH3:2])=[CH:9][C:10]=1[CH3:14]

Participants

4

Reactant 2

HCID 220413931,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxalineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 222683017-Bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxalineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline (516 mg, 2.22 mmol) and tetrabutylammonium tribromide (1.18 g, 2.45 mmol) in anhydrous dichloromethane (20 mL) was stirred at room temperature for 4 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40S cartridge, eluting with 5% ethyl acetate/95% hexane, to give 7-bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline as a white solid (480 mg, 70%).

Workup

  1. washThe solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL)
  2. dry with materiala saturated aqueous solution of NaCl (150 mL), dried over MgSO4
  3. filtrationfiltered
  4. customRemoval of the solvent under reduced pressure
  5. customgave a solid which
  6. customwas purified by column chromatography
  7. washeluting with 5% ethyl acetate/95% hexane

Sources & evidence

ORD record
ord-486fb668dd094e34ae65c14770bef439
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

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