Phenol → 1-[6-Methyl-2-(4-methylphenyl)-4-quinolinyl]-4-piperidinecarboxamide

HRID 638302Notes

Reaction equation

HRID 638302 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:3]=1.[NH:20]1[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]1.C1(O)C=CC=CC=1>O>[CH3:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[CH:3]=[C:2]2[N:20]1[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 136039044-Chloro-6-methyl-2-(4-methylphenyl)quinoline

Product 1

HCID 136039321-[6-Methyl-2-(4-methylphenyl)-4-quinolinyl]-4-piperidinecarboxamideYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.2 g of 4-chloro-6-methyl-2-(4-methylphenyl)quinoline, 3.06 g (24 mmol) of isonipecotamide, and 6 g of phenol was stirred and heated in an oil bath at 160° for 4 hr. It was then cooled and diluted with water. Crystallization was induced by the addition of ethanol and scratching. The solid was collected and washed with ether to give 3.18 g of crude product. Recrystallization from n-butanol gave off-white prisms, mp 242°-244° dec.

Workup

  1. temperatureheated in an oil bath at 160° for 4 hr
  2. temperatureIt was then cooled
  3. customCrystallization
  4. additionwas induced by the addition of ethanol
  5. customThe solid was collected
  6. washwashed with ether

Sources & evidence

ORD record
ord-15a4146d0cf9443290012e1486c1e332
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

Loading…