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

HRID 1076911Notes

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+].[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)[CH2:11][C:10]=3[CH:9]=2)=[O:7])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 30 g. (0.07 mole) of 2,7-bis(5-chlorovaleryl)-xanthene, 2 g of potassium iodide, 100 ml. of piperidine, and 200 ml. of tetrahydrofuran was heated and stirred at 100°C. for 24 hours. After cooling, the tetrahydrofuran was evaporated off and the resulting mixture was poured into water. The resulting solid was filtered off and recrystallized twice from heptane to give the desired product after drying at 80°C. under vacuum. M.P. 129°-130°C.

Workup

additionA mixture of 30 g
temperatureAfter cooling
customthe tetrahydrofuran was evaporated off
additionthe resulting mixture was poured into water
filtrationThe resulting solid was filtered off
customrecrystallized twice from heptane

Sources & evidence

ORD record: ord-6c5a6223dbc0454eaa870725c351cf93
Source dataset: uspto-grants-1976_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03957989

Reaction notes

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