Potassium Iodide → HCID 21514082, compound

HRID 1576110Notes

Reaction equation

HRID 1576110 reaction equation
[Cl:1][CH:2]([F:14])[CH2:3][CH:4]([F:13])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.CN(C)C=O>[ClH:1].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:23][CH2:24][N:25]([CH:2]([F:14])[CH2:3][CH:4]([F:13])[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:6])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 21514133HCID 21514133, compound

Product 1

HCID 21514082HCID 21514082, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of γ-chloro-2,4-difluorobutyrophenone (14.2 g), 4-(4-chlorophenyl)-4-hydroxypiperidine (13.8 g), anhydrous potassium carbonate (9.0 g), potassium iodide (0.5 g) and dimethylformamide (170 ml) was heated for 20 hours at 90° - 110°C. After cooling, the reaction mixture was diluted with water and extracted with ether. The ethereal extract was sufficiently washed with water, dried over anhydrous sodium sulfate, treated with hydrogen chloride and then concentrated. Trituration and recrystallization of the residue from methanol gave γ-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-2,4-difluorobutyrophenone hydrochloride. M.P. 245°C (decomposition).

Workup

  1. temperaturewas heated for 20 hours at 90° - 110°C
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washwas sufficiently washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. additiontreated with hydrogen chloride
  8. concentrationconcentrated
  9. customTrituration and recrystallization of the residue from methanol

Sources & evidence

ORD record
ord-fb3c24514c5441aea7c4f097c95b3747
Source dataset
uspto-grants-1976_09
Patent number
US03979390

Reaction notes

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