4-[3-(Trifluoromethyl)phenyl]-4-piperidinol → HCID 20393855, compound

HRID 1862916Notes

Reaction equation

HRID 1862916 reaction equation
Cl.[F:2][C:3]([F:25])([F:24])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([NH:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=3)=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH2:38]1[C:43]([OH:54])([C:44]2[CH:49]=[CH:48][CH:47]=[C:46]([C:50]([F:53])([F:52])[F:51])[CH:45]=2)[CH2:42][CH2:41][NH:40][CH2:39]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:53][C:50]([F:51])([F:52])[C:46]1[CH:45]=[C:44]([C:43]2([OH:54])[CH2:42][CH2:41][N:40]([C:19](=[O:21])[C:18]3[CH:17]=[CH:16][C:15]([NH:14][C:8]4[C:7]5[C:12](=[CH:13][C:4]([C:3]([F:2])([F:25])[F:24])=[CH:5][CH:6]=5)[N:11]=[CH:10][CH:9]=4)=[CH:23][CH:22]=3)[CH2:39][CH2:38]2)[CH:49]=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 516892Sodium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 13544839HCID 13544839, compound

Product 1

HCID 20393855HCID 20393855, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 mmol of 4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoic acid hydrochloride in dry dimethylformamide is stirred in a nitrogen atmosphere at 20°-25° C.; 1.1 mmol of carbonyl diimidazole is added and the mixture stirred further for 1 hour. 4-Hydroxy-4-[(3-trifluoromethyl)phenyl]piperidine (1.1 mmol) is then added and the reaction mixture is stirred for 20 hours, then poured into aqueous sodium bicarbonate and is extracted with methylene chloride. The organic extract is dried over anhydrous sodium sulfate and concentrated in vacuo. The concentrate is crystallized and recrystallized from methylene chloride to give 86% yield of 4-[3-(trifluoromethyl)phenyl]-4-hydroxy-1-[4-[[7-(trifluoromethyl)-4-quinolinyl]amino]benzoyl]piperidine of m.p. 278°-279° C.

Workup

  1. stirringthe reaction mixture is stirred for 20 hours
  2. extractionis extracted with methylene chloride
  3. extractionThe organic extract
  4. dry with materialis dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe concentrate is crystallized
  7. customrecrystallized from methylene chloride

Sources & evidence

ORD record
ord-467b802b1ff3443faedf154d80658e8e
Source dataset
uspto-grants-1979_09
Patent number
US04166853

Reaction notes

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