Potassium Iodide → Hydrochloric Acid

HRID 1657561Notes

Reaction equation

HRID 1657561 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:27])[CH2:10][CH2:11][CH2:12][NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1.[H-].[Na+].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[Cl:38]CCCC(C1C=CC(F)=CC=1)=O>C1C=CC=CC=1.O.CN(C)C=O>[ClH:38].[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:27])[CH2:10][CH2:11][CH2:12][NH:13][C@H:14]2[CH2:15][CH2:16][C@H:17]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH2:18][CH2:19]2)=[CH:7][CH:8]=1

Participants

10

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 24758Sodium hydrideHCID 178479689HCID 178479689, compound

Product 2

HCID 313Hydrochloric AcidHCID 178479689HCID 178479689, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2 g. of trans 4-(p-fluorophenyl)cyclohexylamine hydrochloride (I) (prepared as in Example 20) in 30 ml. of dimethylformamide, 0.36 g. of 56% sodium hydride in mineral oil is added. Following about 25 minutes of stirring, there is added successively, 2.42 g. of potassium carbonate, 1.49 g. of potassium iodide and 2.18 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone. The mixture is stirred in an oil bath at 90° for about 18 hours, allowed to cool and then dissolved in benzene and water. The organic layer is washed thoroughly with water and brine and then taken to dryness. The residue is dissolved in 80 ml. of methanol; 40 ml. of 2.5N hydrochloric acid is added, mixture stirred for about 1 hour and then concentrated under vacuum. The precipitated solid is collected on a filter. Two recrystallizations from methanol: 2.5N hydrochloric acid gives pure trans 4'-fluoro-4-{[ 4-(p-fluorophenyl)cyclohexyl]amine}butyrophenone hydrochloride (I), m.p. 193° to 197° C.

Workup

  1. additionTo a suspension of 2 g
  2. additionthere is added successively
  3. stirringThe mixture is stirred in an oil bath at 90° for about 18 hours
  4. temperatureto cool
  5. washThe organic layer is washed thoroughly with water and brine
  6. dissolutionThe residue is dissolved in 80 ml
  7. additionof 2.5N hydrochloric acid is added
  8. stirringmixture stirred for about 1 hour
  9. concentrationconcentrated under vacuum
  10. customThe precipitated solid is collected on a filter
  11. customTwo recrystallizations from methanol

Sources & evidence

ORD record
ord-d44a6ce5dc474560a086930ec0ce37c5
Source dataset
uspto-grants-1976_06
Patent number
US03960961

Reaction notes

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