Potassium Carbonate → 2-(1-(4-[4-(benzyloxy)phenyl]butyl}-1H-imidazol-2-yl)-1-ethanol

HRID 2084378Notes

Reaction equation

HRID 2084378 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[OH:20][CH2:21][CH2:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH2:22][CH2:21][OH:20])=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 150160802-(1H-imidazol-2-yl)ethan-1-olHCID 22259342Benzyl 4-(4-iodobutyl)phenyl ether

Product 1

HCID 222593132-(1-(4-[4-(benzyloxy)phenyl]butyl}-1H-imidazol-2-yl)-1-ethanolYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl 4-(4-iodobutyl)phenyl ether (14.29 g), 2-(2-hydroxyethyl)imidazole (13.1 g), and potassium carbonate (5.39 g) were stirred in DMF (390 ml)at 60° C. for 16 hours. After cooling, the insoluble matter was filtered off; the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and saturated saline. Under reduced pressure, the solvent was distilled off; the residue was purified by column chromatography (eluent: ethyl acetate-methanol=19:1→9:1). The eluate was recrystallized from ethyl acetate-methanol to yield the titled compound (10.99 g) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and saturated saline
  6. distillationUnder reduced pressure, the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate-methanol=19:1→9:1)
  8. customThe eluate was recrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-bef30653f713421196f68db0ec2654d5
Source dataset
uspto-grants-2004_04
Patent number
US06716863B2

Reaction notes

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