Potassium Iodide → N-(2,6-dimethylphenyl)-N-(1-ethyl-4-piperidinyl)benzeneacetamide

HRID 28149Notes

Reaction equation

HRID 28149 reaction equation
I[CH2:2][CH3:3].[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N:12]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C1C=CC=CC=1>[CH3:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[N:12]([CH:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH3:3])[CH2:24][CH2:23]1)[C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 23339027N-(2,6-dimethylphenyl)-N-(4-piperidinyl)benzeneacetamide

Product 1

HCID 23339023N-(2,6-dimethylphenyl)-N-(1-ethyl-4-piperidinyl)benzeneacetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4 parts of iodoethane, 5 parts of N-(2,6-dimethylphenyl)-N-(4-piperidinyl)benzeneacetamide, 5 parts of sodium carbonate, a few crystals of potassium iodide in 200 parts of benzene is stirred and refluxed for 23 hours. The reaction mixture is filtered hot and the filtrate is evaporated in vacuo. The solid residue is crystallized from 1,1'-oxybisethane, yielding 2 parts of N-(2,6-dimethylphenyl)-N-(1-ethyl-4-piperidinyl)-benzeneacetamide; mp. 86.5° C.

Workup

  1. temperaturerefluxed for 23 hours
  2. filtrationThe reaction mixture is filtered hot
  3. customthe filtrate is evaporated in vacuo
  4. customThe solid residue is crystallized from 1,1'-oxybisethane

Sources & evidence

ORD record
ord-aab89c7a23234d3ba95280b803fe0545
Source dataset
uspto-grants-1980_09
Patent number
US04225606

Reaction notes

Loading…