Potassium Carbonate → HCID 18349617, compound

HRID 378613Notes

Reaction equation

HRID 378613 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Cl:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH2:18][N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 18349584N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)propylamine

Product 1

HCID 18349617HCID 18349617, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Methyl bromoacetate (2.1 g) was added to a stirred mixture of N-[2-(4-chlorophenoxy)ethyl]-3-(imidazol-1-yl)propylamine (3.87 g) and anhydrous potassium carbonate (5.73 g) in dry acetone (180 ml). The mixture was stirred and boiled under reflux for 7 hours, then left to stand at ambient temperature for 18 hours then hot filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica using ethyl acetate/triethylamine, 9 to 1 as the mobile phase. The product was obtained as an oil which was dissolved in ether, and extracted into 5M hydrochloric acid. The acid extracts were basified with 5M sodium hydroxide solution and the product extracted into ether to give methyl N-[2-(4-chlorophenoxy)ethyl]-N-[3-(imidazol-1-yl)propyl]glycinate as an oil.

Workup

  1. temperatureunder reflux for 7 hours
  2. waitleft
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was purified by chromatography on silica
  5. customThe product was obtained as an oil which
  6. extractionextracted into 5M hydrochloric acid
  7. extractionthe product extracted into ether

Sources & evidence

ORD record
ord-70beb7a9859447858598999c5834ff18
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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