Potassium Iodide → HCID 20368874, compound

HRID 616768Notes

Reaction equation

HRID 616768 reaction equation
Br[CH:2]([F:16])[CH2:3][CH:4]([N+:13]([O-:15])=[O:14])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[OH:17][C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C1(C)C=CC=CC=1>[OH:17][C:18]1([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=2)[CH2:23][CH2:22][N:21]([CH:2]([F:16])[CH2:3][CH:4]([N+:13]([O-:15])=[O:14])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:6])[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 20368903HCID 20368903, compound

Product 1

HCID 20368874HCID 20368874, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 9.4 g of γ-bromo-4-fluoro-2-nitrobutyrophenone, 7.1 g of 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine, 4.0 of potassium carbonate, a catalytic amount of potassium iodide and 60 ml of toluene was stirred at room temperature for 10 hours. The resulting mixture was diluted with water and extracted with toluene-ethyl acetate (1:1), and the organic layer was extracted with cold 30% hydrochloric acid. The hydrochloric acid layer was washed with toluene, made alkaline with 20% aqueous sodium hydroxide solution under cooling and extracted with ethyl acetate. The extracts were washed with water, dried over anhydrous sodium sulfate and concentrated to yield 6.4 g of γ-[4-hydroxy-4-(3-trifluoromethylphenyl)piperidino]-4-fluoro-2-nitrobutyrophenone as a residual oil, which was converted into its hydrochloride by a conventional manner. M.P. 200°-209° C.

Workup

  1. extractionextracted with toluene-ethyl acetate (1:1)
  2. extractionthe organic layer was extracted with cold 30% hydrochloric acid
  3. washThe hydrochloric acid layer was washed with toluene
  4. temperatureunder cooling
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5f22b2714de142adb9a134bbaad39528
Source dataset
uspto-grants-1978_02
Patent number
US04075346

Reaction notes

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