Hydrochloric Acid → 4-[2,2-Bis(4-fluorophenyl)ethyl]pyridine hydrochloride

HRID 1460245Notes

Reaction equation

HRID 1460245 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)(O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[P].I.[ClH:26]>C(O)(=O)C.CO.CCOCC>[ClH:26].[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24841Hydrogen iodideHCID 5462309PhosphorusHCID 15020359alpha,alpha-Bis(4-fluorophenyl)-4-pyridineethanol

Product 1

HCID 199830744-[2,2-Bis(4-fluorophenyl)ethyl]pyridine hydrochlorideYield 87%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 15.05 g (0.048 mole) of α,α-bis(4-fluorophenyl)-4-pyridineethanol, 3.2 g (0.1 mole) of phosphorus and 50 ml of 56.9% hydrogen iodide in 150 ml of glacial acetic acid was heated at reflux for 11 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in a mixture of methanol and ether, and an excess of ethereal hydrogen chloride was added. The solvent was removed in vacuo, and the residue was recrystallized from a mixture of acetonitrile and ether to give 13.89 g (87% yield) of title compound as a white, crystalline solid, mp 197°-199° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 11 hr
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  5. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give an oil
  8. customThe solvent was removed in vacuo
  9. customthe residue was recrystallized from a mixture of acetonitrile and ether

Sources & evidence

ORD record
ord-ed7e1f09f45a4e02a3738e8c7dd0d436
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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