Potassium Iodide → HCID 21528589, compound

HRID 1658666Notes

Reaction equation

HRID 1658666 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:32])[CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]([OH:31])([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.Cl.FC1C=CC(C(=O)CCC[N:45]2[CH2:50][CH2:49][CH:48](C(O)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:47][CH2:46]2)=CC=1.[I-].[K+]>N1CCCCC1>[OH:31][C:18]([CH:15]1[CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:45]3[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:3][CH:4]=2)=[O:32])[CH2:13][CH2:14]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 2061821-Butanone, 1-(4-fluorophenyl)-4-(4-(hydroxydiphenylmethyl)-1-piperidinyl)-, hydrochlorideHCID 206183HCID 206183, compound

Product 1

HCID 21528589HCID 21528589, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A mixture of 15 g (0.035 mole) of 4'-fluoro-4-[4-(α-hydroxy-α-phenylbenzyl)piperidino]butyrophenone, the free base of the compound of Example 1, and a small amount of potassium iodide in 100 ml of piperidine was refluxed for 22 hours. The unreacted piperidine was removed under vacuum, and the remaining residue was triturated with water, the water decanted, and the residue dissolved in methanol and added to a large amount of water. The resulting precipitate was dissolved in a large volume of ether, dried over magnesium sulfate, treated with charcoal and filtered. The filtrate was concentrated to a 50 ml volume and cooled, yielding a product which was recrystallized from ether to give the title compound, M.P. 137.5°-139° C.

Workup

  1. customThe unreacted piperidine was removed under vacuum
  2. customthe remaining residue was triturated with water
  3. customthe water decanted
  4. dissolutionthe residue dissolved in methanol
  5. additionadded to a large amount of water
  6. dissolutionThe resulting precipitate was dissolved in a large volume of ether
  7. dry with materialdried over magnesium sulfate
  8. additiontreated with charcoal
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated to a 50 ml volume
  11. temperaturecooled
  12. customyielding a product which
  13. customwas recrystallized from ether

Sources & evidence

ORD record
ord-a5257876677443108786e040a31e448f
Source dataset
uspto-grants-1976_06
Patent number
US03965257

Reaction notes

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