Toluene → HCID 21514080, compound

HRID 1576116Notes

Reaction equation

HRID 1576116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:27])[CH2:13][CH2:12][N:11]([CH:14]([F:26])[CH2:15][CH:16](F)[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(C)C=CC=CC=1>O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:27])[CH2:13][CH2:12][N:11]([CH:14]([F:26])[CH2:15][CH:16]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8082PiperidineHCID 21514083HCID 21514083, compound

Product 1

HCID 21514080HCID 21514080, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluorobutyrophenone (1.5 g), piperidine (15.0 g) and toluene (50 ml) was heated for 23 hours under refluxing. The reaction mixture was diluted with water and extracted with toluene. The extract was sufficiently washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was treated with hydrochloric acid in ethanol-ether, and the resulting product was recrystallized from isopropanol to yield γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-4-fluoro-2-piperidinobutyrophenone hydrochloride. M.P 218° - 220°C (decomposition).

Workup

  1. temperaturewas heated for 23 hours
  2. temperatureunder refluxing
  3. extractionextracted with toluene
  4. washThe extract was sufficiently washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with hydrochloric acid in ethanol-ether
  8. customthe resulting product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-344d0466e10f4899b58ce17ad5484e5d
Source dataset
uspto-grants-1976_09
Patent number
US03979390

Reaction notes

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