Water → HCID 13151505, compound

HRID 1648866Notes

Reaction equation

HRID 1648866 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][CH:28]=[CH:29][C:24]=3[NH:23][C:22]2=[O:30])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[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][CH:28]=[CH:29][C:24]=5[NH:23][C:22]4=[O:30])[CH2:19][CH2:20]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 13151500HCID 13151500, compound

Product 1

HCID 13151505HCID 13151505, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5.0 g of trans-2-(4-fluorophenyl)-4-(iodomethyl)tetrahydrofuran, 4.2 g of 1-(4-piperidyl)benzimidazolin-2-one and 2.5 g of potassium carbonate in 80 ml of dimethylformamide is heated with stirring at 60°-70° C. for 42 hours. The reaction mixture is then poured into water and extracted with ethyl acetate. The extract is washed three times with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. Isopropyl ether is added to the residue, and the crystals precipitated are collected by filtration and recrystallized from ethanol to give 5.1 g of 1-[1-(trans-2-(4-fluorophenyl)-tetrahydro-4-furylmethyl)-4-piperidyl]benzimidazolin-2-one as colorless needles, melting at 154°-155° C. The corresponding hydrochloride melts at 239° C. with decomposition.

Workup

  1. temperatureis heated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed three times with water
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. additionIsopropyl ether is added to the residue
  7. customthe crystals precipitated
  8. filtrationare collected by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9cea8133b27d4afe854dc46358fb0f21
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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