Water → HCID 86739107, compound

HRID 1648868Notes

Reaction equation

HRID 1648868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([CH2:13]I)[CH2:10][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][C:28]([Cl:30])=[CH:29][C:24]=3[NH:23][C:22]2=[O:31])[CH2:17][CH2:16]1.[C:32](=[O:35])([O-:34])[O-].[K+].[K+].O>CN(C)C=O>[C:8]([OH:31])(=[O:9])/[CH:12]=[CH:11]\[C:32]([OH:34])=[O:35].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([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)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 13151500HCID 13151500, compound

Product 1

HCID 86739107HCID 86739107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5.2 g of trans-2-(4-fluorophenyl)-4-(iodomethyl)tetrahydrofuran, 4.3 g of 1-(4-piperidyl)-5-chloro-benzimidazolin-2-one and 2.3 g of potassium carbonate in 50 ml of dimethylformamide is heated with stirring at 70° 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 dissolved in a small amount of chloroform, and a solution of 0.8 g of maleic acid in ethanol is added thereto. The crystals precipitated are collected by filtration and recrystallized from methanol to give 1-[1-(trans-2-(4-fluorophenyl)-tetrahydro-4-furylmethyl)-4-piperidyl]-5-chloro-benzimidazolin-2-one maleate, melting at 208.5°-209° C.

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. dissolutionThe residue is dissolved in a small amount of chloroform
  7. additiona solution of 0.8 g of maleic acid in ethanol is added
  8. customThe crystals precipitated
  9. filtrationare collected by filtration
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8a86ef657d12404ca5e4f35fa4e3035b
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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