1-Chloro-2-(diethylamine)ethane hydrochloride → Diethyl [2-(4-imidazol-1-yl-phenoxy)ethyl]amine

HRID 232323

Reaction equation

HRID 232323 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[K+].Cl.[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20]Cl)[CH3:17]>CO>[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1)[CH3:17]

Participants

5

Reactant 3

HCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 14797Potassium HydroxideHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 14555626Diethyl [2-(4-imidazol-1-yl-phenoxy)ethyl]amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 4-(1H-imidazol-1-yl)phenol (4.02 g, 25.1 mmol) in methanol (100 mL) containing potassium hydroxide (3.52 g, 62.74 mmol). Add 2-diethylaminoethyl chloride hydrochloride to this mixture and heat to reflux under nitrogen overnight. Cool the mixture and concentrate in vacuo. Dissolve the residue in water (50mL) and adjust the pH to 13 with 1N NaOH solution. Wash with 2×100 mL of methylene chloride, combine, dry (Na2SO4) and concentrate in vacuo. This residue is dissolved in ethanol and 37% hydrochloric acid is added until pH=1.0. Concentration affords crystals which are recrystallized from isopropanol/ethanol (ca. 4+1). Drying at 80° C. for 5 hr at 1.0 mm give the title compound.

Workup

  1. temperatureto reflux under nitrogen overnight
  2. temperatureCool the mixture
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the residue in water (50mL)
  5. washWash with 2×100 mL of methylene chloride
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate in vacuo
  8. dissolutionThis residue is dissolved in ethanol
  9. addition37% hydrochloric acid is added until pH=1.0
  10. concentrationConcentration
  11. customaffords crystals which
  12. customare recrystallized from isopropanol/ethanol (ca. 4+1)
  13. customDrying at 80° C. for 5 hr at 1.0 mm

Sources & evidence

ORD record
ord-49aa9a410d3d4590af99be4b72679df0
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

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