Potassium cyanate → HCID 70524050, compound

HRID 1648871Notes

Reaction equation

HRID 1648871 reaction equation
[ClH:1].Cl.Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:15][C@@H:14]([CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[NH2:30])[CH2:19][CH2:18]3)[CH2:13][O:12]2)=[CH:7][CH:6]=1.[O-:31][C:32]#N.[K+]>C(O)C>[ClH:1].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:15][C@@H:14]([CH2:16][N:17]3[CH2:18][CH2:19][CH:20]([N:23]4[C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=5[NH:30][C:32]4=[O:31])[CH2:21][CH2:22]3)[CH2:13][O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 70471640HCID 70471640, compound

Product 1

HCID 70524050HCID 70524050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.56 g of 1-[cis-2-(4-fluorophenyl)-tetrahydro-4-furylmethyl]-4-(2-aminoanilino)piperidine trihydrochloride and 2.0 g of potassium cyanate in 100 ml of ethanol is heated under reflux with stirring for 8 hours. The ethanol is then distilled off under reduced pressure, and 10 ml of 10% aqueous sodium hydroxide solution and 50 ml of water are added to the residue 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 ethanol, and ethanolic hydrochloric acid is added thereto. The crystals precipitated are collected by filtration and recrystallized from ethanol-water to give 1-[1-(cis-2-(4-fluorophenyl)-tetrahydro-4-furylmethyl)-4-piperidyl]benzimidazolin-2-one hydrochloride, melting at 276° C. with decomposition.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. distillationThe ethanol is then distilled off under reduced pressure, and 10 ml of 10% aqueous sodium hydroxide solution and 50 ml of water
  4. additionare added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. dissolutionThe residue is dissolved in a small amount of ethanol, and ethanolic hydrochloric acid
  10. additionis added
  11. customThe crystals precipitated
  12. filtrationare collected by filtration
  13. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-7246ed82af334d6ba318a59f3fb32cb3
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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