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Potassium Iodide → 5-(diallylamino)-1-[7-[5-(diallylamino)pentanoyl]-9H-xanthen-2-yl]pentan-1-one

HRID 1076908
Notes
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Reaction equation

HRID 1076908 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)[CH2:11][C:10]=2[CH:9]=1)=[O:7].[I-].[K+].[CH2:31]([NH:34][CH2:35][CH:36]=[CH2:37])[CH:32]=[CH2:33]>O1CCCC1>[CH2:31]([N:34]([CH2:35][CH:36]=[CH2:37])[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][N:34]([CH2:35][CH:36]=[CH2:37])[CH2:31][CH:32]=[CH2:33])=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1)=[O:7])[CH:32]=[CH2:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31279DiallylamineHCID 123402842,7-Bis(5-chlorovaleryl)-xanthene

Product 1

HCID 5154045-(diallylamino)-1-[7-[5-(diallylamino)pentanoyl]-9H-xanthen-2-yl]pentan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 41.9 g (0.1 mole) of 2,7-bis(5-chlorovaleryl)-xanthene, 2 g of potassium iodide, 100 ml of diallylamine and 200 ml. of tetrahydrofuran was heated and stirred at 120°C. for 24 hours. After cooling, the reaction mixture was filtered and the filtrate evaporated to dryness. The resulting residue was cooled, dissolved in 10% HCl, extracted with diethyl ether and made alkaline. The product was extracted with methylene chloride, evaporated to dryness, recrystallized six times from heptane and dried in vacuo to give the desired product. M.P. 54°-55°C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. temperatureThe resulting residue was cooled
  5. dissolutiondissolved in 10% HCl
  6. extractionextracted with diethyl ether
  7. extractionThe product was extracted with methylene chloride
  8. customevaporated to dryness
  9. customrecrystallized six times from heptane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-2deafccd569744edaca47e0df8d63394
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03957989

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes