2-Chloroethanol → N-Ethyl-N-(2-hydroxyethyl)-N-[2-(4-methylphenoxy)ethyl]-amine

HRID 232313Notes

Reaction equation

HRID 232313 reaction equation
Cl[CH2:2][CH2:3][OH:4].[CH2:5]([NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH3:6].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:5]([N:7]([CH2:2][CH2:3][OH:4])[CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH3:6]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 20031351N-Ethyl-2-(4-methylphenoxy)ethanamine

Product 1

HCID 20031320N-Ethyl-N-(2-hydroxyethyl)-N-[2-(4-methylphenoxy)ethyl]-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 0.90 g (011 mol) 2-chloroethanol to a solution of 2.0 g (0.11 mol) N-ethyl-N-[2-(4-methylphenoxy)ethyl]amine and 1.7 g (012 mol) potassium carbonate in 50 mL methanol. Stir at room temperature for 24 hr. After this time, remove the solvents in vacuo and dissolve the residue in 25 mL water. Adjust the aqueous to pH=8 with 5% sodium bicarbonate solution and extract 3×50 mL methylene chloride. Dry the combined organics over sodium sulfate and evaporate the solvent to obtain the desired product.

Workup

  1. customAfter this time, remove the solvents in vacuo
  2. dissolutiondissolve the residue in 25 mL water
  3. extractionextract 3×50 mL methylene chloride
  4. dry with materialDry the combined organics over sodium sulfate
  5. customevaporate the solvent

Sources & evidence

ORD record
ord-f2eb8d7c4d324159a69739c911fcf09a
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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