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

HRID 1578656Notes

Reaction equation

HRID 1578656 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 is heated at reflux for 68 hours with stirring, then filtered. Upon cooling, the mixture is diluted with 500 ml of water, and the resulting semi-solid is dissolved in ether, washed repeatedly with water and dried over magnesium sulfate. The ethereal solution is treated with ethereal HCl to give N-ethyl-3,6-bis(4-piperidinobutyryl)carbazole dihydrochloride hemihydrate, which is recrystallized from methanol-ethyl acetate, M.P. 138°-142°C.

Workup

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

Sources & evidence

ORD record
ord-df51a94990ed4c7f98850525d5428132
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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