Potassium Iodide → HCID 23339043, compound

HRID 26758Notes

Reaction equation

HRID 26758 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([N:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].I[CH2:34][CH2:35][CH3:36]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:11]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[CH:12]2[CH2:17][CH2:16][N:15]([CH2:34][CH2:35][CH3:36])[CH2:14][CH2:13]2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 336431-Iodopropane2×HCID 233389954-chloro-N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide

Product 1

HCID 23339043HCID 23339043, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a stirred and refluxing mixture of 5 parts of 4-chloro-N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide, 5 parts of sodium carbonate, 0.4 parts of potassium iodide and 200 parts of butanol is added 4.7 parts of 1-iodopropane and the whole is stirred and refluxed for 22 hours. Then a second portion of 4.5 parts of 1-iodopropane is added and stirring and refluxing is continued for 27h.30. The reaction mixture is cooled, filtered and the filtrate is evaporated. The semi-solid residue is dissolved in methylbenzene. The solution is filtered from some impurities and the filtrate is evaporated again. The residue is crystallized from 1,1'-oxybisethane at -10° C.; yielding 0.9 parts of 4-chloro-N-(4-chlorophenyl)-N-(1-propyl-4-piperidinyl)benzeneacetamide; mp. 118.6° C.

Workup

  1. temperaturerefluxing
  2. stirringthe whole is stirred
  3. temperaturerefluxed for 22 hours
  4. stirringstirring
  5. temperaturerefluxing
  6. temperatureThe reaction mixture is cooled
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. dissolutionThe semi-solid residue is dissolved in methylbenzene
  10. filtrationThe solution is filtered from some impurities
  11. customthe filtrate is evaporated again
  12. customThe residue is crystallized from 1,1'-oxybisethane at -10° C.

Sources & evidence

ORD record
ord-873fbda636df455a949aad67303deb6c
Source dataset
uspto-grants-1979_04
Patent number
US04151286

Reaction notes

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