Potassium Iodide → 9-Ethyl-3,6-bis(4-piperidinobutyryl)carbazole dihydrochloride hemihydrate

HRID 268141Notes

Reaction equation

HRID 268141 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][Cl:20])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Cl)[CH:8]=2)[CH3:2].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.[I-].[K+]>O1CCOCC1>[OH2:21].[ClH:20].[ClH:20].[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:8]=2)[CH3:2].[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:22](=[O:27])[CH2:23][CH2:24][CH2:25][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:8]=2)[CH3:2].[ClH:20].[ClH:20]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8082PiperidineHCID 123317903,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

Product 1

HCID 1317100349-Ethyl-3,6-bis(4-piperidinobutyryl)carbazole dihydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 19.5 g (0.048 mole) of N-ethyl-3,6-bis(4-chlorobutyryl)carbazole, 34.0 g (0.4 mole) of piperidine and 2.0 g of potassium iodide in 250 ml of p-dioxane was heated at reflux for 68 hours with stirring, then filtered. Upon cooling the mixture was diluted with 500 ml of water, and the resulting semi-solid was dissolved in ether, washed repeatedly with water and dried over magnesium sulfate. The ethereal solution was treated with ethereal HCl to give the desired product which was recrystallized from methanol-ethyl acetate. M.P. 138°-142°C, λmaxEtOH 258, E1cm1% 699.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 68 hours
  3. filtrationfiltered
  4. temperatureUpon cooling the mixture
  5. additionwas diluted with 500 ml of water
  6. dissolutionthe resulting semi-solid was dissolved in ether
  7. washwashed repeatedly with water
  8. dry with materialdried over magnesium sulfate
  9. additionThe ethereal solution was treated with ethereal HCl

Sources & evidence

ORD record
ord-cf66182d5dd948b58da127a207b0e7ba
Source dataset
uspto-grants-1976_03
Patent number
US03946021

Reaction notes

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