Sodium Iodide → HCID 13151510, compound

HRID 1648867Notes

Reaction equation

HRID 1648867 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([CH2:13]Br)[O:9]2)=[CH:4][CH:3]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[NH:23][C:22]2=[O:30])[CH2:17][CH2:16]1.[I-].[Na+].[C:33](=[O:36])([O-:35])[O-].[K+].[K+]>CN(C)C=O.O>[C:8]([OH:30])(=[O:9])/[CH:12]=[CH:11]/[C:33]([OH:35])=[O:36].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][CH:10]([CH2:13][N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:19][CH2:20]3)[O:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 13151502HCID 13151502, compound

Product 1

HCID 13151510HCID 13151510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.59 g of 2-(4-fluorophenyl)-5-(bromomethyl)tetrahydrofuran, 2.17 g of 1-(4-piperidyl)benzimidazolin-2-one, 1.5 g of sodium iodide and 1.38 g of potassium carbonate in 30 ml of dimethylformamide is heated with stirring at 50°-60° C. for 3 hours. The reaction mixture is then poured into water and extracted with chloroform. The extract is washed twice with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluant. The thus obtained colorless oil is dissolved in ethanol, and fumaric acid is added thereto. The crystals precipitated are collected by filtration and recrystallized from ethanol to give 1-[1-(2-(4-fluorophenyl)-tetrahydro-5-furylmethyl)-4-piperidyl]benzimidazolin-2-one fumarate as colorless needles, melting at 200°-201° C.

Workup

  1. temperatureis heated
  2. extractionextracted with chloroform
  3. washThe extract is washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel with chloroform eluant
  7. dissolutionThe thus obtained colorless oil is dissolved in ethanol
  8. additionfumaric acid is added
  9. customThe crystals precipitated
  10. filtrationare collected by filtration
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f648f5e0229a49b492096d3d0cb3268b
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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