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

HRID 534967Notes

Reaction equation

HRID 534967 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]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[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]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 667512494-(2-tert-butylphenyl)-N-(4-hydroxyphenyl)piperazine-1-carboxamide

Product 1

HCID 66751108Methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-(2-tert-butylphenyl)-N-(4-hydroxyphenyl)piperazine-1-carboxamide (Example 174, 0.290 g, 0.82 mmol), methyl bromoacetate (0.163 g, 1.07 mmol), and potassium carbonate (0.227 g, 1.64 mmol) in DMF (3 mL) was stirred at room temperature for 24 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to give the crude product, which was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 50:50) to provide methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}amino)phenoxy]acetate (0.260 g, 75%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure
  5. customto give the crude product, which
  6. customwas purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 50:50)

Sources & evidence

ORD record
ord-235f9132060844a5861898d485eaed68
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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