Potassium Iodide → HCID 14407141, compound

HRID 1193709Notes

Reaction equation

HRID 1193709 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:22][C:23]1(Cl)[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]1(Cl)[O:30][CH2:31][CH2:32][CH2:33]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(O)CCC.CO>[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]([CH2:33][CH2:32][CH2:31][O:30][C:24]3[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:23]=3[Cl:22])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 132505444-[Bis(4-fluorophenyl)methyl]piperidineHCID 21272273HCID 21272273, compound

Product 1

HCID 14407141HCID 14407141, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-[bis(4-fluorophenyl)methyl]piperidine (free base 6.90 g, 0.024 mole), 1,3-dichloro-1,2-dichloro-2-(3-chloropropoxy)benzene (5.72 g, 0.024 mole), and potassium carbonate (5.54 g, 0.04 mole) was heated overnight at gentle reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The reaction was stripped to dryness. The residue was partitioned several times between chloroform and water. The chloroform layer was dried, filtered, and solvent removed to give an oil. The oil was placed in the refrigerator overnight in 50 ml of methanol. A white solid was obtained and dried in vacuo overnight at 80° C. A yield of 3.26 g (27.7%) of white crystalline solid, m.p. 101.5°-103° C. was obtained.

Workup

  1. temperaturewas heated overnight
  2. customThe residue was partitioned several times between chloroform and water
  3. dry with materialThe chloroform layer was dried
  4. filtrationfiltered
  5. customsolvent removed
  6. customto give an oil
  7. customA white solid was obtained
  8. customdried in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-310ba595f6994f84aceda0227687bb2e
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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