Dimethylamine → 3,6-bis(4-dimethylaminobutyryl)-N-ethylcarbazole

HRID 268524

Reaction equation

HRID 268524 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH2:26][CH3:27])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][C:15]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Cl)=[CH:14][CH:13]=3)=[O:6].C([N:30]1[C:42]2C=CC=CC=2C2[C:31]1=CC=CC=2)C.ClCCCC(Cl)=O.[CH3:50][NH:51][CH3:52].[I-].[K+].[C:55]([OH:62])(=[O:61])/[CH:56]=[CH:57]/[C:58]([OH:60])=[O:59]>O1CCOCC1>[CH3:50][N:51]([CH3:52])[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH2:26][CH3:27])[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][C:15]([C:20](=[O:25])[CH2:21][CH2:22][CH2:23][N:30]([CH3:42])[CH3:31])=[CH:14][CH:13]=3)=[O:6].[C:55]([O-:62])(=[O:61])/[CH:56]=[CH:57]/[C:58]([O-:60])=[O:59]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 4875Potassium IodideHCID 6836N-ethyl carbazoleHCID 783704-Chlorobutyryl chlorideHCID 444972Fumaric AcidHCID 123317903,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

Product 2

HCID 4613193,6-bis(4-dimethylaminobutyryl)-N-ethylcarbazoleHCID 5460307Fumarate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 15.8 g (0.039 mole) of 3,6-bis(4-chlorobutyryl)-N-ethylcarbazole, prepared from N-ethylcarbazole and 4-chlorobutyryl chloride, 75 ml of 40% aqueous dimethylamine and 2 g of potassium iodide in 175 ml of p-dioxane is heated in a reaction bomb with stirring for 44 hours. The reaction mixture is concentrated to one-half its original volume in vacuo and diluted with 500 ml of water. The semi-solid which separates is dissolved in ether and washed repeatedly with water and dried over magnesium sulfate to give the free base which is treated with fumaric acid and recrystallized from butanone to give 3,6-bis(4-dimethylaminobutyryl)-N-ethylcarbazole bis acid fumarate. M.P. 94°-98°C.

Workup

  1. temperatureis heated in a reaction bomb
  2. concentrationThe reaction mixture is concentrated to one-half its original volume in vacuo
  3. additiondiluted with 500 ml of water
  4. dissolutionThe semi-solid which separates is dissolved in ether
  5. washwashed repeatedly with water
  6. dry with materialdried over magnesium sulfate
  7. customto give the free base which
  8. customrecrystallized from butanone

Sources & evidence

ORD record
ord-98dbf57019ff4ad687fba3e1257f67bf
Source dataset
uspto-grants-1976_03
Patent number
US03947593

Linked notes

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