Sodium Iodide → HCID 13253888, compound

HRID 1648870Notes

Reaction equation

HRID 1648870 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][O:11][CH:10]([CH2:13]Br)[CH2:9]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][C:28]([Cl:30])=[CH:29][C:24]=3[NH:23][C:22]2=[O:31])[CH2:17][CH2:16]1.[I-].[Na+].[C:34](=[O:37])([O-:36])[O-].[K+].[K+]>CN(C)C=O.O>[C:12]([OH:11])(=[O:31])/[CH:8]=[CH:9]\[C:34]([OH:36])=[O:37].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][O:11][CH:10]([CH2:13][N:15]3[CH2:16][CH2:17][CH:18]([N:21]4[C:25]5[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=5[NH:23][C:22]4=[O:31])[CH2:19][CH2:20]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 20481061HCID 20481061, compound

Product 1

HCID 13253888HCID 13253888, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.1 g of 4-(4-fluorophenyl)-2-(bromomethyl)tetrahydrofuran, 3.5 g of 1-(4-piperidyl)-5-chloro-benzimidazolin-2-one, 2.5 g of sodium iodide and 2.0 g of potassium carbonate in 50 ml of dimethylformamide is heated with stirring at 60° C. for 24 hours. The reaction mixture is then poured into water and extracted with ethyl acetate. The extract is washed 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 oil is treated with maleic acid. The crystalline precipitate is collected by filtration and recrystallized from ethanol to give 1-[1-(4-(4-fluorophenyl)-tetrahydro-2-furylmethyl)-4-piperidyl]-5-chloro-benzimidazolin-2-one maleate, melting at 200°-201° C. with decomposition.

Workup

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed 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. additionThe thus obtained oil is treated with maleic acid
  8. filtrationThe crystalline precipitate is collected by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-67dc207f96164958b88fc9ad2c6228d5
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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