1-Chloro-2-(diethylamine)ethane hydrochloride → 3,6-Bis(2-diethylaminoethoxy)-N-ethylcarbazole dihydrochloride

HRID 268519Notes

Reaction equation

HRID 268519 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18][C:19](=O)[CH3:20])=[CH:12][CH:11]=3)(=O)[CH3:2].[ClH:24].C([N:27]([CH2:31][CH3:32])[CH2:28][CH2:29][Cl:30])C.C[O-].[Na+]>ClC1C=CC=CC=1>[ClH:30].[ClH:24].[CH2:31]([N:27]([CH2:28][CH3:29])[CH2:2][CH2:1][O:4][C:5]1[CH:17]=[CH:16][C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:11]([C:7]=2[CH:6]=1)=[CH:12][C:13]([O:18][CH2:19][CH2:20][N:9]([CH2:10][CH3:11])[CH2:8][CH3:7])=[CH:14][CH:15]=3)[CH3:32]

Participants

5

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 10942334Sodium MethoxideHCID 12331788N-ethyl-3,6-carbazolediol diacetate

Product 1

HCID 123317093,6-Bis(2-diethylaminoethoxy)-N-ethylcarbazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 15.5 g (0.05 mole) of N-ethyl-3,6-carbazolediol diacetate, 17.2 g (0.1 mole) of 2-diethylaminoethylchloride hydrochloride, 10.8 g (0.2 mole) of sodium methoxide and 400 ml of chlorobenzene is refluxed for 24 hours. Upon cooling, the reaction mixture is filtered, and the filtrate is washed with several portions of water, dried over anhydrous magnesium sulfate, diluted with ether and acidified with ethereal HCl. The resulting precipitate is separated and recrystallized from methanol-ethyl acetate to give 3,6-bis(2-diethylaminoethoxy)-N-ethylcarbazole dihydrochloride. M.P. 208°-210°C.

Workup

  1. temperatureis refluxed for 24 hours
  2. temperatureUpon cooling
  3. filtrationthe reaction mixture is filtered
  4. washthe filtrate is washed with several portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additiondiluted with ether
  7. customThe resulting precipitate is separated
  8. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-87f53c089b064b76b8ddc6cee4b42cac
Source dataset
uspto-grants-1976_03
Patent number
US03947593

Reaction notes

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