Potassium Iodide → N-(4-chlorophenyl)-N-(1-cyclopentyl-4-piperidinyl)benzeneacetamide

HRID 1704424Notes

Reaction equation

HRID 1704424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].Br[CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8728Bromocyclopentane2×HCID 10340Sodium CarbonateHCID 162188N-(4-Chlorophenyl)-N-4-piperidinylbenzeneacetamide

Product 1

HCID 20334078N-(4-chlorophenyl)-N-(1-cyclopentyl-4-piperidinyl)benzeneacetamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

to a stirred and warm (40° C.) mixture of 5 parts of N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide, 5 parts of sodium carbonate, a few crystals of potassium iodide and 200 parts of n.butanol is added 3.75 parts of bromocyclopentane and the whole is stirred and refluxed for 21h.30. Then a second portion of 5 parts of bromocyclopentane is added and stirring at reflux temperature is continued for another 30 hours. The reaction mixture is cooled, filtered and the filtrate is evaporated. The oily residue solidifies on triturating in 1,1'-oxybisethane. The solid product is filtered off and crystallized from 1,1'-oxybisethane, yielding 1.1 parts of N-(4-chlorophenyl)-N-(1-cyclopentyl-4-piperidinyl)benzeneacetamide; mp. 139.5° C.

Workup

  1. temperaturewarm
  2. stirringthe whole is stirred
  3. temperaturerefluxed for 21h.30
  4. stirringstirring
  5. temperatureat reflux temperature
  6. temperatureThe reaction mixture is cooled
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. customon triturating in 1,1'-oxybisethane
  10. filtrationThe solid product is filtered off
  11. customcrystallized from 1,1'-oxybisethane

Sources & evidence

ORD record
ord-5aa1a86702c54625ac14c721da92f521
Source dataset
uspto-grants-1978_11
Patent number
US04126689

Reaction notes

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