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Potassium Iodide → 5-((3-(3-Pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 393634
Notes
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Reaction equation

HRID 393634 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH:5][CH:6]=[C:7]1[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]1=[O:16].[N:22]1([CH2:27][CH2:28][CH2:29]Cl)[CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.O>[N:22]1([CH2:27][CH2:28][CH2:29][O:1][C:2]2[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[NH:5][CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:10]([CH3:14])([CH3:15])[O:9][C:8]2=[O:16])[CH2:26][CH2:25][CH2:24][CH2:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 226465515-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 226466245-((3-(3-Pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-((3-hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3dioxane-4,6-dione (10 g, 34.1 mmol), (prepared as described for the starting material in Example 3), 3-(pyrrolidin-1-yl)propyl chloride (7.55 g, 51.1 mmol), (J. Am. Chem. Soc. 1955, 77, 2272), potassium carbonate (7.06 g, 51.1 mmol) and potassium iodide (600 mg, 3.41 mmol) in DMF (100 ml) was heated at 80° C. for 2 hours. The mixture was poured into water (800 ml) and the precipitate was collected by filtration. The solid was dissolved in methylene chloride and the organic solution was washed with brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was dissolved in ether and the insoluble materials were removed by filtration. The volatiles were removed by evaporation and the residue was precipitated by trituration with petroleum ether, collected by filtration and dried under vacuum to give 5-((3-(3-pyrrolidin-1-ylpropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (5.1 g, 37%).

Workup

  1. custom(prepared
  2. filtrationthe precipitate was collected by filtration
  3. dissolutionThe solid was dissolved in methylene chloride
  4. washthe organic solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. dissolutionThe residue was dissolved in ether
  8. customthe insoluble materials were removed by filtration
  9. customThe volatiles were removed by evaporation
  10. customthe residue was precipitated by trituration with petroleum ether
  11. filtrationcollected by filtration
  12. customdried under vacuum

Sources & evidence

ORD record
ord-139ab7d4fd21498db212a6ccf5dc1608
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809097B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes