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

HRID 534980Notes

Reaction equation

HRID 534980 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]=[CH:21][NH:22][CH:23]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].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]=[CH:21][N:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:23]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178440808HCID 178440808, compound

Product 1

HCID 66751284Methyl (4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-1H-imidazol-1-yl)acetateYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)-4-(1H-imidazol-4-ylcarbonyl)piperazine (Example 3, 0.60 g, 1.92 mmol), methyl bromoacetate (0.35 g, 2.3 mmol) and potassium carbonate (0.80 g, 5.8 mmol) in N,N-dimethylformamide (6.4 mL) was stirred at room temperature 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 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 (0.49 g, 66%) as a white powder.

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 silica gel column chromatography (hexane/ethyl acetate 50:50 to 0:100

Sources & evidence

ORD record
ord-a0f5658c468a4d3eb4a49f0eb1457e65
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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