Piperidine, 1-(2-chloroethyl)-, hydrochloride → N-ethyl-3,6-bis(2-piperidinoethoxy)carbazole dihydrochloride

HRID 1578648Notes

Reaction equation

HRID 1578648 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].[N:25]1(CC[Cl:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C[O-].[Na+]>ClC1C=CC=CC=1>[ClH:33].[ClH:24].[CH2:22]([N:9]1[C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH2:2][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([O:18][CH2:19][CH2:20][N:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1)[CH:14]=2)[CH3:23]

Participants

5

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 10942334Sodium MethoxideHCID 12331788N-ethyl-3,6-carbazolediol diacetate

Product 1

HCID 12331710N-ethyl-3,6-bis(2-piperidinoethoxy)carbazole dihydrochloride

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 15.5 g (0.05 mole) of N-ethyl-3,6-carbazolediol diacetate, 18.4 g (0.1 mole) of 2-piperidinoethylchloride 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 collected and recrystallized from methanol-ethyl acetate to give N-ethyl-3,6-bis(2-piperidinoethoxy)carbazole dihydrochloride, M.P. 248°-250°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 collected
  8. customrecrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-794f540646d9402fb3d55423882ae4b0
Source dataset
uspto-grants-1976_02
Patent number
US03937833

Reaction notes

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