Potassium Iodide → HCID 14407141, compound

HRID 1709894Notes

Reaction equation

HRID 1709894 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[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[O:30][CH2:31][CH2:32][CH2:33]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CO.C(O)CCC>[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 23036379HCID 23036379, compound

Product 1

HCID 14407141HCID 14407141, compound

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-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 m l of 1-butanol containing potassium iodide (0.2 g). The reaction was concentrated 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. concentrationThe reaction was concentrated to dryness
  3. customThe residue was partitioned several times between chloroform and water
  4. dry with materialThe chloroform layer was dried
  5. filtrationfiltered
  6. customsolvent removed
  7. customto give an oil
  8. customA white solid was obtained
  9. customdried in vacuo overnight at 80° C
  10. customA yield of 3.26 g (27.7%) of white, crystalline solid, m.p. 101.5°-103° C., was obtained

Sources & evidence

ORD record
ord-b1d60f7c0b3a429bb7b32fa50e4f2e13
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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