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

HRID 1076908Notes

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]

Participants

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

temperatureAfter cooling
filtrationthe reaction mixture was filtered
customthe filtrate evaporated to dryness
temperatureThe resulting residue was cooled
dissolutiondissolved in 10% HCl
extractionextracted with diethyl ether
extractionThe product was extracted with methylene chloride
customevaporated to dryness
customrecrystallized six times from heptane
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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