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

HRID 236761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236761
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturewarm
  2. stirringthe whole is stirred
  3. temperaturerefluxed for 21h
  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

Quellen und Nachweise

ORD-Eintrag
ord-adc4355ff09a4496a25b2aa2ce118de2
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04157393

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