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

HRID 1076911
Notes
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Reaction equation

HRID 1076911 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 123402842,7-Bis(5-chlorovaleryl)-xanthene

Product 1

HCID 5154035-(1-piperidyl)-1-[7-[5-(1-piperidyl)pentanoyl]-9H-xanthen-2-yl]pentan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. additionA mixture of 30 g
  2. temperatureAfter cooling
  3. customthe tetrahydrofuran was evaporated off
  4. additionthe resulting mixture was poured into water
  5. filtrationThe resulting solid was filtered off
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes