Phenol → 1-[2(4-Chlorophenyl)-6-fluoro 4-quinolinyl]-4-piperidinecarboxamide

HRID 638265Notes

Reaction equation

HRID 638265 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([Cl: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>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:4]2[CH:3]=[C:2]([N:20]3[CH2:28][CH2:27][CH:23]([C:24]([NH2:26])=[O:25])[CH2:22][CH2:21]3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=3)[N:5]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 37724-PiperidinecarboxamideHCID 136038954-Chloro-2-(4-chlorophenyl)-6-fluoroquinoline

Product 1

HCID 136039111-[2(4-Chlorophenyl)-6-fluoro 4-quinolinyl]-4-piperidinecarboxamideYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.4 g (15 mmol) of 4-chloro-2-(4-chlorophenyl)-6-fluoroquinoline, 3.9 g (30 mmol) of isonipecotamide, and 6 g of phenol was stirred and heated in an oil bath at 165°-180° for 2 hr. It was then cooled and diluted with 100 ml of water. Crystallization was induced by scratching. The solid was collected and washed with ether to give 5.2 g of crude product, mp 258°-260° dec. Recrystallization from pyridine/water gave off-white needles, mp 259°-261°.

Workup

  1. temperatureheated in an oil bath at 165°-180° for 2 hr
  2. temperatureIt was then cooled
  3. customCrystallization
  4. customThe solid was collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-f16293001c164706afe44d933734b962
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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