Sodium hydride → 2-[4-(1H-Imidazol-1-yl)phenoxy]ethanamine dihydrochloride

HRID 232301

Reaction equation

HRID 232301 reaction equation
[H-].[Na+].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[ClH:15].[Cl:16][CH2:17][CH2:18][NH2:19]>CN(C)C=O>[ClH:16].[ClH:15].[N:3]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:17][CH2:18][NH2:19])=[CH:10][CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 823151-(p-Hydroxyphenyl)imidazoleHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 145556582-[4-(1H-Imidazol-1-yl)phenoxy]ethanamine dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a cold solution of 11.3 g (0.235 mol) 50% sodium hydride in 50 mL dimethylformamide add 15 g (0.094 mol) 4-(1H-imidazol-1-yl)phenol portionwise. Maintain the temperature below 0° C. during the addition. After the addition, add dropwise a solution of 10.89 g (0.094 mol) 2-chloroethylamine hydrochloride in 50 mL dimethylformamide. After addition, warm the reaction mixture to 70° C., and heat for 24 hours. After this time, cool the reaction mixture and quench with water. Filter the solids and wash the mother liquors with 2X250 mL ether, 3X250 mL methylene chloride. Dry the methylene chloride layers over Na2SO4 and evaporate the solvents. Dissolve the resultant oil in methanolic HCl and evaporate the solvent to obtain the title compound.

Workup

  1. temperatureMaintain the temperature below 0° C.
  2. additionduring the addition
  3. additionAfter the addition
  4. additionAfter addition
  5. temperatureheat for 24 hours
  6. temperatureAfter this time, cool the reaction mixture
  7. customquench with water
  8. filtrationFilter the solids
  9. washwash the mother liquors with 2X250 mL ether, 3X250 mL methylene chloride
  10. dry with materialDry the methylene chloride layers over Na2SO4
  11. customevaporate the solvents
  12. dissolutionDissolve the resultant oil in methanolic HCl
  13. customevaporate the solvent

Sources & evidence

ORD record
ord-40e707f0835846fbb29773fd4f30478d
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Linked notes

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