Potassium Carbonate → Tert-butyl 4-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)piperazine-1-carboxylate

HRID 1023338Notes

Reaction equation

HRID 1023338 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[CH:23]([O:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:25][CH:23]([O:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:2][C:3]2[CH:22]=[CH:21][C:6]([CH2:7][N:8]3[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]3)=[CH:5][CH:4]=2)=[CH:29][CH:28]=1)[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 820014-IsopropoxyphenolHCID 67379301Tert-butyl 4-(4-(chloromethyl)benzyl)piperazine-1-carboxylate

Product 1

HCID 67328500Tert-butyl 4-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)piperazine-1-carboxylateYield 99.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-[4-(chloromethyl)benzyl]piperazine-1-carboxylate (4.00 g) in DMF (25 mL) were added 4-isopropoxyphenol (2.81 g) and K2CO3 (3.40 g) at room temperature, then the reaction mixture was stirred for 2 days. The reaction mixture was diluted with H2O, and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1 to 1/1) to afford tert-butyl 4-(4-{[4-(propan-2-yloxy)phenoxy]methyl}benzyl)piperazine-1-carboxylate as a colorless solid (5.42 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1 to 1/1)

Sources & evidence

ORD record
ord-f39faea518fa41879472501cc3b744a6
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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