Potassium Iodide → 1,1'-(9H-Carbazole-3,6-diyl)bis[4-(piperidin-1-yl)butan-1-one]

HRID 268142Notes

Reaction equation

HRID 268142 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][C:15]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Cl)=[CH:14][CH:13]=3)=[O:6].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[I-].[K+]>O1CCCC1>[N:26]1([CH2:2][CH2:3][CH2:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[NH:11][C:12]4[C:17]([C:18]=3[CH:19]=2)=[CH:16][C:15]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:14][CH:13]=4)=[O:6])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 123317891,1'-(9H-Carbazole-3,6-diyl)bis(4-chlorobutan-1-one)

Product 1

HCID 123317151,1'-(9H-Carbazole-3,6-diyl)bis[4-(piperidin-1-yl)butan-1-one]

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.0 g (0.04 mole) of 3,6-bis(4-chlorobutyryl)carbazole, 85.0 g (1.0 mole) of piperidine and 2.0 g of potassium iodide in 15 ml of tetrahydrofuran was heated at 110°C in a reaction bomb for 24 hours with stirring. Upon cooling the reaction mixture was filtered and diluted with 700 ml of ice water. The resulting solid was washed with water, dried over magnesium sulfate and recrystallized from chloroformpetroleum ether (75°-90°C) and then from acetone to give the desired product. M.P. 171°-173°C, λmaxEtOH 259, E1cm1% 894.

Workup

  1. temperatureUpon cooling the reaction mixture
  2. filtrationwas filtered
  3. additiondiluted with 700 ml of ice water
  4. washThe resulting solid was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customrecrystallized from chloroformpetroleum ether (75°-90°C)

Sources & evidence

ORD record
ord-5266eb537de14ebd8c6f9d1abd900ed8
Source dataset
uspto-grants-1976_03
Patent number
US03946021

Reaction notes

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