Potassium Iodide → HCID 21272261, compound

HRID 1193686Notes

Reaction equation

HRID 1193686 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=1[O:36][CH3:37].C(=O)(O)[O-].[Na+].[I-].[K+].[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49]>C(O)CCC.CCOCC.CO>[C:45]([OH:52])(=[O:51])/[CH:46]=[CH:47]/[C:48]([OH:50])=[O:49].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=3[O:36][CH3:37])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidine

Product 1

HCID 21272261HCID 21272261, compound

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent3×

Procedure

A mixture of 58.26 g (0.203 mole) of 4-[bis(4-fluorophenyl)methyl]piperidine, 54.5 g (0.225 mole) of 1-chloro-3-(4-acetyl-2-methoxyphenoxy)propane, 18.7 g (0.223 mole) of sodium bicarbonate and 1.2 g (0.0072 mole) of potassium iodide in 800 ml of 1-butanol was refluxed for 16 hr. The hot reaction mixture was filtered, and the solvent was removed in vacuo from the filtrate. 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. The oil was dissolved in 600 ml of anhydrous ether, and 4.91 g of a solid was collected at room temperature. The ether solution was then treated with a solution of 30.2 g (0.26 mole) of fumaric acid in methanol. Anhydrous ether was added and 99.88 g (77.7%), m.p. 160°-163° C. of title compound was isolated. This was recrystallized from isopropanol-diethyl ether, (2.5 g, 0.0216 mole of additional fumaric acid was added) to give 2 crops of title compound. [Crop I-44.15 g, m.p. 163°-164.5° C.; Crop II-38.75 g, m.p. 161°-163° C⟧ An additional 10.00 g (8.786%), m.p. 159°-162° C. of title compound collected from the original ether-methanol filtrate.

Workup

  1. temperaturewas refluxed for 16 hr
  2. filtrationThe hot reaction mixture was filtered
  3. customthe solvent was removed in vacuo from the filtrate
  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. custom4.91 g of a solid was collected at room temperature

Sources & evidence

ORD record
ord-ad837523e6f24a4b9c6087ef35232ace
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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