Triethylamine → HCID 11131919, compound

HRID 1457061Notes

Reaction equation

HRID 1457061 reaction equation
[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:16][CH2:15][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=3[C:5]=2[CH2:4]1.C(N(CC)CC)C.[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1>O1CCCC1.[OH-].[Na+]>[CH3:1][N:2]([CH3:17])[CH:3]1[CH2:16][CH2:15][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([NH:14][C:30](=[O:31])[C:29]4[CH:33]=[CH:34][C:26]([F:25])=[CH:27][CH:28]=4)=[CH:10][C:9]=3[C:5]=2[CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 9839408HCID 9839408, compound

Product 1

HCID 11131919HCID 11131919, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 0.132 gm (0.57 mMol) of N,N-dimethyl-8-amino-1,2,3,4-tetrahydro-2-dibenzofuranamine in 5 mL of tetrahydrofuran were added 1.5 mL of triethylamine followed by 0.10 mL (0.13 gm, 0.85 mMol) of 4-fluorobenzoyl chloride. The resulting mixture was stirred at room temperature for 90 minutes at which time the reaction mixture was diluted with 0.1N aqueous sodium hydroxide. This aqueous solution was extracted with dichloromethane and the organic phases were washed sequentially with water and saturated aqueous sodium chloride. The dichloromethane solution was dried over sodium sulfate and concentrated under reduced pressure. This residue was dissolved in dilute aqueous tartaric acid and then washed with dichloromethane. The aqueous phase made basic with aqueous sodium carbonate and was then extracted with dichloromethane. These dichloro-methane extracts were combined and concentrated under reduced pressure. The residue was subjected to radial chromatography (silica gel, 2 mm), eluting with 5% methanol (containing 5% ammonium hydroxide) in chloro-form. Fractions containing product were combined and concentrated under reduced pressure. The residue was crystallized from toluene/hexane to provide 0.130 gm (64%) of the title compound in two crops.

Workup

  1. extractionThis aqueous solution was extracted with dichloromethane
  2. washthe organic phases were washed sequentially with water and saturated aqueous sodium chloride
  3. dry with materialThe dichloromethane solution was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThis residue was dissolved in dilute aqueous tartaric acid
  6. washwashed with dichloromethane
  7. extractionwas then extracted with dichloromethane
  8. concentrationconcentrated under reduced pressure
  9. washeluting with 5% methanol (containing 5% ammonium hydroxide) in chloro-form
  10. additionFractions containing product
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was crystallized from toluene/hexane

Sources & evidence

ORD record
ord-ce6a930a60594adc9ebb9825bb4391b9
Source dataset
uspto-grants-1998_12
Patent number
US05846995

Reaction notes

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