Propylamine → N-(2-(2,4,6-Trichlorophenoxy)ethyl)-1-propanamine

HRID 2352549Notes

Reaction equation

HRID 2352549 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13].C(N(CC)CC)C.[CH2:21]([NH2:24])[CH2:22][CH3:23]>C(O)C>[CH2:21]([NH:24][CH2:2][CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13])[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 135651032-(2-Bromoethoxy)-1,3,5-trichlorobenzene

Product 1

HCID 3842173N-(2-(2,4,6-Trichlorophenoxy)ethyl)-1-propanamineYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of sodium hydroxide (7.8 g, 0.195 mol) in water (20 ml) was added to a solution of 2,4,6-trichlorophenol (38.0 g, 0.192 mol) in ethanol (200 ml). 1,2-dibromoethane (47 g, 0.25 mol) was then added and the resultant mixture was refluxed overnight. On cooling, the solid was filtered off and the filtrate concentrated under reduced pressure. Ether was added to the residue and the solution was then washed with dilute sodium hydroxide solution and dried over anhydrous magnesium sulphate. After removal of the solvent by evaporation, the residue was recrystallised from ethanol to give 1-bromo-2-(2,4,6-trichlorophenoxy)ethane as a white solid (39.4 g). A mixture of the 1-bromo-2-(2,4,6-trichlorophenoxy) ethane (20.0 g, 0.066 mol), triethylamine (6.7 g, 0.066 mol) and propylamine (3.9 g, 0.066 mol) in ethanol (500 ml) was then refluxed overnight. After removal of the solvent by evaporation, the residue was dissolved in ether, washed with water and dried (MgSO4). Evaporation of the solvent left an oil which, after flash chromatography on silica gel using chloroform as the eluant, yielded N-propyl-N-2-(2,4,6-trichlorophenoxy)ethylamine as an oil (12.6 g).

Workup

  1. temperaturewas then refluxed overnight
  2. customAfter removal of the solvent
  3. customby evaporation
  4. dissolutionthe residue was dissolved in ether
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. waitleft an oil which

Sources & evidence

ORD record
ord-a5fe570962bd40ef88c9f7b55b491d1d
Source dataset
uspto-grants-1989_10
Patent number
US04877802

Reaction notes

Loading…