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

HRID 378614Notes

Reaction equation

HRID 378614 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-04adeb650ce440eb8f7c17e5e1667502
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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