Water → HCID 20492819, compound

HRID 434520Notes

Reaction equation

HRID 434520 reaction equation
Cl[CH2:2][C:3]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[O:5][N:4]=1.[Cl:15][C:16]1[CH:31]=[CH:30][C:19]2[N:20]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:21](=[O:23])[NH:22][C:18]=2[CH:17]=1.C(=O)([O-])[O-:33].[K+].[K+].[I-].[K+].[OH2:40]>C(Cl)(Cl)Cl.C(O)C>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2([OH:5])[O:40][NH:4][C:3]([CH2:2][N:27]3[CH2:26][CH2:25][CH:24]([N:20]4[C:19]5[CH:30]=[CH:31][C:16]([Cl:15])=[CH:17][C:18]=5[NH:22][C:21]4=[O:23])[CH2:29][CH2:28]3)=[C:7]2[OH:33])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 962WaterHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 20492817HCID 20492817, compound

Product 1

HCID 20492819HCID 20492819, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

3-Chloromethyl-5-(4-fluorophenyl)-4,5-dihydroisoxazole (40 g), 52 g of 4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine, 30 g of potassium carbonate, 15 g of potassium iodide and 1 liter of ethanol are heated to a temperature of 70° to 75° C. with stirring for 48 hours. The reaction mixture is then filtered and the mother liquor is condensed under reduced pressure. To the residue are added 800 ml of chloroform and 500 ml of water and the mixture is stirred. The organic layer is separated off, washed with water and dried on magnesium sulfate, and the solvent is distilled off. To the resulting residue are added 130 ml of acetone and 100 ml of isopropyl ether. The crystals thus precipitated are filtered and recrystallized from a mixture of acetone (400 ml) and isopropyl ether (450 ml), to give 67.5 g of 1-[5-(4-fluorophenyl)-4,5-dihydroxyisoxazol-3-ylmethyl]-4-(5-chloro-2-oxo-1-benzimidazolinyl)piperidine having a melting point of 163° to 164° C. Hydrochloride of this compound melts at 216° C. (decomposition).

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customcondensed under reduced pressure
  3. stirringthe mixture is stirred
  4. customThe organic layer is separated off
  5. washwashed with water
  6. customdried on magnesium sulfate
  7. distillationthe solvent is distilled off
  8. additionTo the resulting residue are added 130 ml of acetone and 100 ml of isopropyl ether
  9. customThe crystals thus precipitated
  10. filtrationare filtered
  11. customrecrystallized from a mixture of acetone (400 ml) and isopropyl ether (450 ml)

Sources & evidence

ORD record
ord-10b5f36c5bd041878d3fb13b0401fb22
Source dataset
uspto-grants-1983_08
Patent number
US04397853

Reaction notes

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