Potassium Iodide → HCID 21419593, compound

HRID 441648Notes

Reaction equation

HRID 441648 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[CH:21]=[CH:20][C:19]2[O:18][C:17]3[C:12](=[CH:13][C:14]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26]Cl)=[CH:15][CH:16]=3)[S:11][C:10]=2[CH:9]=1)=[O:7].[I-].[K+].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>O1CCCC1>[N:31]1([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]2[CH:21]=[CH:20][C:19]3[O:18][C:17]4[C:12](=[CH:13][C:14]([C:22](=[O:28])[CH2:23][CH2:24][CH2:25][CH2:26][N:31]5[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)=[CH:15][CH:16]=4)[S:11][C:10]=3[CH:9]=2)=[O:7])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 21419582HCID 21419582, compound

Product 1

HCID 21419593HCID 21419593, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 35 g (0.08 mole) of 2,8-bis(5-chlorovaleryl)phenoxathiin, 2 g potassium iodide, 100 ml piperidine and 100 ml tetrahydrofuran is heated for 24 hours with stirring in a Parr bomb at 110° C. After cooling the mixture is filtered and washed with tetrahydrofuran, and the filtrate is evaporated to dryness. The residue is cooled and diluted with water. The mixture is extracted twice with ether, the ether extracts combined and filtered. The filtrate is evaporated to dryness, cooled and diluted with pentane followed by filtering off of the solid, washing with pentane and drying. The residue is recrystallized from isopropanol to yield 2,8-bis(5-piperidinovaleryl)phenoxathiin, M.P. 128.5°-129.5° C.

Workup

  1. temperatureis heated for 24 hours
  2. temperatureAfter cooling the mixture
  3. filtrationis filtered
  4. washwashed with tetrahydrofuran
  5. customthe filtrate is evaporated to dryness
  6. temperatureThe residue is cooled
  7. additiondiluted with water
  8. extractionThe mixture is extracted twice with ether
  9. filtrationfiltered
  10. customThe filtrate is evaporated to dryness
  11. temperaturecooled
  12. additiondiluted with pentane
  13. filtrationby filtering off of the solid
  14. washwashing with pentane
  15. customdrying
  16. customThe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-9b1f670a3c5945e68dc08e8ffb91fa93
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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