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

HRID 441644Notes

Reaction equation

HRID 441644 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 is heated at 110° C. in a reaction bomb for 24 hours with stirring. Upon cooling, the reaction mixture is filtered and diluted with 700 ml of ice water. The resulting solid is washed with water, dried over magnesium sulfate and recrystallized from chloroform-petroleum ether (75°-90° C.) and then from acetone to give 3,6-bis(4-piperidinobutyryl)carbazole, M.P. 171°-173° C.

Workup

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

Sources & evidence

ORD record
ord-11d30cb4e5f24d8581ce69307642abdd
Source dataset
uspto-grants-1977_08
Patent number
US04041165

Reaction notes

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