Water → 187401-16-7

HRID 986927Notes

Reaction equation

HRID 986927 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[N:7]=[C:6]([CH2:14][OH:15])[CH:5]=[N:4][C:3]1=2.C(N(CC)CC)C.O.C(OCC)(=O)C.CCCCCC>ClCCl>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[N:7]=[C:6]([CH:14]=[O:15])[CH:5]=[N:4][C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10775307HCID 10775307, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10751321187401-16-7Yield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7.7 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethylquinoxaline-2-methanol in 120 ml of dichloromethane was then added dropwise to the reaction mixture and the resulting mixture-was stirred for 15 minutes. To the reaction mixture were added with 35.1 ml of triethylamine, followed by stirring for 5 minutes. After the reaction mixture was raised to room temperature and stirred for 15 minutes, water was added and the resulting mixture was extracted with dichloromethane. The organic layer was successively washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column (developing solvent: 10% ethyl acetate/n-hexane), whereby 6.7 g of the title compound were obtained as a pale yellow solid.

Workup

  1. stirringby stirring for 5 minutes
  2. stirringstirred for 15 minutes
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. washThe organic layer was successively washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue so obtained

Sources & evidence

ORD record
ord-efa73725d91249bd92cc3b48f471ee1a
Source dataset
uspto-grants-2003_10
Patent number
US06630463B2

Reaction notes

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