Potassium Iodide → HCID 12331755, compound

HRID 614855Notes

Reaction equation

HRID 614855 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:25]=[CH:24][C:10]2[O:11][C:12]3[CH:17]=[CH:16][C:15]([C:18](=[O:23])[CH2:19][CH2:20][CH2:21]Cl)=[CH:14][C:13]=3[C:9]=2[CH:8]=1)=[O:6].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[I-].[K+]>CC(=O)CC>[N:26]1([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:25]=[CH:24][C:10]3[O:11][C:12]4[CH:17]=[CH:16][C:15]([C:18](=[O:23])[CH2:19][CH2:20][CH2:21][N:26]5[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]5)=[CH:14][C:13]=4[C:9]=3[CH:8]=2)=[O:6])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 12331793HCID 12331793, compound

Product 1

HCID 12331755HCID 12331755, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 17.0 g (0.045 mole) of 2,8-bis(4-chlorobutyryl)dibenzofuran, 68.0 g (0.8 mole) of piperidine and 2.0 g of potassium iodide in 500 ml of butanone was heated at reflux for 72 hours then filtered. The filtrate was concentrated to one-half its original volume then diluted with 600 ml of water. The resulting semi-solid was purified by chromatography on neutral alumina using methylenechloride as the eluant. The solvent was removed from the fraction collected leaving a solid residue which was recrystallized from pentane to give the desired product. M.P. 70°-71° C., λmaxEtOH 251, E1cm1% 1520.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 hours
  3. filtrationthen filtered
  4. concentrationThe filtrate was concentrated to one-half its original volume
  5. additionthen diluted with 600 ml of water
  6. customThe resulting semi-solid was purified by chromatography on neutral alumina
  7. customThe solvent was removed from the fraction
  8. customcollected
  9. customleaving a solid residue which
  10. customwas recrystallized from pentane

Sources & evidence

ORD record
ord-90fa8fb6f2e64d8da1bfe349bc17b9b7
Source dataset
uspto-grants-1979_03
Patent number
US04146624

Reaction notes

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