Water → 2-{N-[2-(4-chlorophenoxy)ethyl]-N-[3-(imidazol-1-yl)propyl]amino}ethanol

HRID 1956851Notes

Reaction equation

HRID 1956851 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:30]=[CH:29][C:11]([O:12][CH2:13][CH2:14][N:15]([CH2:21][CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)[CH2:16][C:17](OC)=[O:18])=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][N:15]([CH2:16][CH2:17][OH:18])[CH2:21][CH2:22][CH2:23][N:24]2[CH:28]=[CH:27][N:26]=[CH:25]2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18349617HCID 18349617, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 183497742-{N-[2-(4-chlorophenoxy)ethyl]-N-[3-(imidazol-1-yl)propyl]amino}ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.23 g) was added to a solution of methyl N-[2-(4-chlorophenoxy)ethyl]-N-[3-(imidazol-1-yl)propyl]glycinate (1.30 g) in THF (30 ml). The mixture was boiled under reflux for 4 hours and then cooled. Water (1 ml) was added followed by 5M sodium hydroxide solution (2 ml) and then more water (2 ml). The mixture was filtered to remove the precipitate using a filtration aid. The filtrate was washed with water, dried and evaporated to give 2-{N-[2-(4-chlorophenoxy)ethyl]-N-[3-(imidazol-1-yl)propyl]amino}ethanol as an oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. customto remove the precipitate
  5. washThe filtrate was washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-c27cdf32150747e98beec4e26df666c8
Source dataset
uspto-grants-1998_07
Patent number
US05780642

Reaction notes

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