Potassium Iodide → HCID 19983119, compound

HRID 1460261Notes

Reaction equation

HRID 1460261 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.Cl[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[O:38])[CH3:37])=[CH:32][C:31]=1[O:39][CH3:40].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:49]([O-:56])(=[O:55])/[CH:50]=[CH:51]/[C:52]([O-:54])=[O:53]>C(O)CCC>[OH2:10].[C:49]([OH:56])(=[O:55])/[CH:50]=[CH:51]/[C:52]([OH:54])=[O:53].[C:36]([C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:28][CH2:27][CH2:26][N:15]2[CH2:16][CH2:17][CH:12]([C:8]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9]([NH2:11])=[O:10])[CH2:13][CH2:14]2)=[C:31]([O:39][CH3:40])[CH:32]=1)(=[O:38])[CH3:37]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5460307FumarateHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 15020370HCID 15020370, compound

Product 1

HCID 19983119HCID 19983119, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of α,α-bis(4-fluorophenyl)-4-piperidineacetamide (6.94 g, 0.021 mole), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.09 g, 0.021 mole), and potassium carbonate (5.53 g, 0.04 mole) was heated overnight at reflux in 350 ml of 1-butanol containing potassium iodide (0.2 g). The mixture was concentrated to dryness. The residue obtained was partitioned between chloroform and water. The chloroform layer was dried (sodium sulfate) and filtered. The solvent was removed to give a yellowish-brown residue. This material was converted to the fumarate, and the salt was recrystallized from methanol-diethyl ether. A white solid was obtained and dried in vacuo overnight at 80° C. This method provided 8.47 g (66.8%) of white, crystalline product, mp 258°-260° C. (dec).

Workup

  1. temperaturewas heated overnight
  2. concentrationThe mixture was concentrated to dryness
  3. customThe residue obtained
  4. customwas partitioned between chloroform and water
  5. dry with materialThe chloroform layer was dried (sodium sulfate)
  6. filtrationfiltered
  7. customThe solvent was removed
  8. customto give a yellowish-brown residue
  9. customthe salt was recrystallized from methanol-diethyl ether
  10. customA white solid was obtained
  11. customdried in vacuo overnight at 80° C
  12. customThis method provided 8.47 g (66.8%) of white, crystalline product, mp 258°-260° C. (dec)

Sources & evidence

ORD record
ord-1f9017279b634d0281123dffb9558a88
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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