Water → Methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-2-methyl-1H-imidazol-1-yl)acetate

HRID 534997Notes

Reaction equation

HRID 534997 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[N:20]=[C:21]([CH3:24])[NH:22][CH:23]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[N:20]=[C:21]([CH3:24])[N:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:23]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178433008HCID 178433008, compound

Product 1

HCID 66751277Methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-2-methyl-1H-imidazol-1-yl)acetateYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(2-tert-butylphenyl)-4-[(2-methyl-1H-imidazol-4-yl)carbonyl]piperazine (0.50 g, 1.53 mmol), methyl bromoacetate (0.28 g, 1.84 mmol) and potassium carbonate (0.63 g, 4.6 mmol) in N,N-dimethylformamide (5 mL) was stirred at 50° C. for 16 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate 50:50). The residue was washed with hexane-ethyl acetate and purified by silica gel column chromatography (hexane/ethyl acetate 50:50 to 0/100 then ethyl acetate/methanol 100/0 to 90/10) to give the title compound (0.25 g, 40%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate 50:50)
  7. washThe residue was washed with hexane-ethyl acetate
  8. custompurified by silica gel column chromatography (hexane/ethyl acetate 50:50 to 0/100

Sources & evidence

ORD record
ord-8cef82f97165466592c8cfef99a0121f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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