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

HRID 1580079Notes

Reaction equation

HRID 1580079 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 was refluxed for 24 hours. Upon cooling, the reaction mixture was filtered, and the filtrate was washed with several portions of water, dried over anhydrous magnesium sulfate, diluted with ether and acidified with ethereal HCl. The resulting precipitate was separated and recrystallized from methanol-ethyl acetate to give the desired product. M.P. 208°-210°C, λmaxEtOH 232, E1cm1% 853.

Workup

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

Sources & evidence

ORD record
ord-c484d72730894fada43ecd2e3f315d66
Source dataset
uspto-grants-1976_01
Patent number
US03932424

Reaction notes

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