Potassium Iodide → HCID 12331755, compound

HRID 1578654Notes

Reaction equation

HRID 1578654 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 is heated at reflux for 72 hours then filtered. The filtrate is concentrated to one-half its original volume then diluted with 600 ml of water. The resulting semi-solid is purified by chromatography on neutral alumina using methylene chloride as the eluant. The solvent is removed from the fraction collected leaving a solid residue which is recrystallized from pentane to give 2,8-bis(4-piperidinobutyryl)dibenzofuran, M.P. 70°-71°C.

Workup

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

Sources & evidence

ORD record
ord-08d1a8354f1848e6a6315bde4d8e1342
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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