1,3-Dibromopropane → N,N'-dimethyl-N,N'-bis(3-hydroxypropyl)-1,3-diaminopropane

HRID 442222Notes

Reaction equation

HRID 442222 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH3:7][NH:8][CH2:9][CH2:10][CH2:11][OH:12].Br[CH2:14][CH2:15][CH2:16]Br>C(O)C>[CH3:7][N:8]([CH2:9][CH2:10][CH2:1][OH:4])[CH2:14][CH2:15][CH2:16][N:8]([CH3:7])[CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 101489863-(Methylamino)-1-propanol

Product 1

HCID 12721803N,N'-dimethyl-N,N'-bis(3-hydroxypropyl)-1,3-diaminopropaneYield 55.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 g of anhydrous potassium carbonate are added to a solution of 9 g of 3-methylaminopropanol and 10 g of 1,3-dibromopropane in 100 ml of ethanol, and the reaction mixture is stirred and refluxed for 24 hours. The mixture is allowed to cool, filtered, the filtrate is evaporated, and the residue is distilled. 6 g of N,N'-dimethyl-N,N'-bis(3-hydroxypropyl)-1,3-diaminopropane are obtained; b.p.: 150°-154° C/2 mmHg, nD20 = 1.4793.

Workup

  1. temperaturerefluxed for 24 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-b6f9df485a2c4b1e8434697c003d3d95
Source dataset
uspto-grants-1977_08
Patent number
US04044146

Reaction notes

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