Sodium Hydroxide → 1-Propanamine, 3-(2-(2-(3,4-dichlorophenyl)ethyl)phenoxy)-N,N-dimethyl-, hydrochloride

HRID 2285538

Reaction equation

HRID 2285538 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1.[H-].[Na+].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24]Cl.[OH-].[Na+]>CN(C)C=O>[ClH:16].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([Cl:17])[CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 205450242-Hydroxy-3',4'-dichlorobibenzyl

Product 1

HCID 30553481-Propanamine, 3-(2-(2-(3,4-dichlorophenyl)ethyl)phenoxy)-N,N-dimethyl-, hydrochlorideYield 142.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.5 g of 2-hydroxy-3',4'-dichlorobibenzyl in 10 ml of dimethylformamide was added 0.23 g of sodium hydride under cooling. The mixture was stirred for 30 minutes and to this was added dropwise 2.2 g of 3-dimethylaminopropyl chloride. The reaction mixture was warmed to about 60° C. and then stirred for 5 hours. Upon completion of the reaction, 2 N-NaOH aqueous solution was added, and the product was extracted with ether. The ether extract was washed well with saturated sodium chloride solution, dried over anhydrous sodium sulfate and then distilled in vacuo to sufficiently remove ether and a small amount of the remaining 3-dimethylaminopropyl chloride. The resultant residue was dissolved in ether and then 20% ethanolic hydrogen chloride was added to yield a precipitate. Recrystallization from ethanol-ether gave 2.6 g (71% yield) of 2-(3-dimethylaminopropoxy)-3',4'-dichlorobibenzyl hydrochloride, m.p. 136°-137° C.

Workup

  1. temperatureunder cooling
  2. stirringstirred for 5 hours
  3. additionwas added
  4. extractionthe product was extracted with ether
  5. extractionThe ether extract
  6. washwas washed well with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled in vacuo to sufficiently remove ether
  9. dissolutionThe resultant residue was dissolved in ether
  10. addition20% ethanolic hydrogen chloride was added
  11. customto yield a precipitate
  12. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-05ceb9f88d0c417c881885af2a0c4e33
Source dataset
uspto-grants-1982_04
Patent number
US04323568

Linked notes

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