Potassium Iodide → Hydrochloric Acid

HRID 1657564Notes

Reaction equation

HRID 1657564 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([C@H:10]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12][CH2:11]2)[CH:4]=1.[H-].[Na+].[K].[I-].[K+].[Cl:22][CH2:23][CH2:24][CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)=[O:27]>CN(C)C=O>[ClH:22].[ClH:1].[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:26](=[O:27])[CH2:25][CH2:24][CH2:23][NH:16][C@H:13]2[CH2:14][CH2:15][C@H:10]([C:5]3[CH:4]=[C:3]([F:2])[CH:8]=[CH:7][C:6]=3[CH3:9])[CH2:11][CH2:12]2)=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 24758Sodium hydrideHCID 5462222PotassiumHCID 178426014HCID 178426014, compound

Product 2

HCID 313Hydrochloric AcidHCID 178426015HCID 178426015, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1.73 g. of trans 4-(p-fluoro-o-tolyl)cyclohexylamine hydrochloride (I) (prepared as in Example 51) in 40 ml. of dimethylformamide, 0.31 g. of 56% sodium hydride in mineral oil is added. After about 1 hour of stirring, 2 g. of potassium, 1.2 g. of potassium iodide and 1.82 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone are added successively. The mixture is stirred in an oil bath at about 90° C. for about 18 hours, allowed to cool and the solvent removed under vacuum by a rotary evaporator. The residue is dissolved in benzene and water; the organic layer is washed with water and brine and then taken to dryness. The residue is dissolved in 30 ml. of methanol, 15 ml. of 2.5N hydrochloric acid is added and the mixture stirred for about 1 hour, then concentrated under vacuum. The precipitated solid is collected on a filter and on recrystallization from methanol:2.5N hydrochloric acid gives pure trans 4'-fluoro-4-{[4-(p-fluoro-o-tolyl)cyclohexyl]amino}butyrophenone hydrochloride (I) melting at 215° to 218° C.

Workup

  1. additionTo a suspension of 1.73 g
  2. stirringThe mixture is stirred in an oil bath at about 90° C. for about 18 hours
  3. temperatureto cool
  4. customthe solvent removed under vacuum by a rotary evaporator
  5. dissolutionThe residue is dissolved in benzene
  6. washthe organic layer is washed with water and brine
  7. dissolutionThe residue is dissolved in 30 ml
  8. additionof 2.5N hydrochloric acid is added
  9. stirringthe mixture stirred for about 1 hour
  10. concentrationconcentrated under vacuum
  11. customThe precipitated solid is collected on
  12. filtrationa filter and on recrystallization from methanol

Sources & evidence

ORD record
ord-396d93dd707c4a1087e8afc71d73f83a
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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