Potassium Iodide → 4-[4-(4-Tert-butyl-phenyl)-piperazin-1-yl]-butyric acid ethyl ester

HRID 511202Notes

Reaction equation

HRID 511202 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:17]([O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23]Br)[CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH2:17]([O:19][C:20](=[O:25])[CH2:21][CH2:22][CH2:23][N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)[CH3:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 7817221-(4-tert-Butylphenyl)piperazine

Product 1

HCID 585764584-[4-(4-Tert-butyl-phenyl)-piperazin-1-yl]-butyric acid ethyl esterYield 84.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(4-tert-butyl-phenyl)-piperazine (1.09 mg; 5.0 mmol), 4-bromo-butyric acid ethyl ester (975 mg; 5.0 mmol), potassium carbonate (691 mg; 5.0 mmol) and potassium iodide (914 mg; 5.5 mmol) in acetonitrile (15 mL) is heated to reflux for 2 hours. The reaction mixture is allowed to attain room temperature and all solids removed by filtration. The filtration residue is washed with acetonitrile and the filtrate concentrated under high vacuum to afford the desired compound (1.41 g; 4.24 mmol).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 2 hours
  3. customto attain room temperature
  4. customall solids removed by filtration
  5. washThe filtration residue is washed with acetonitrile
  6. concentrationthe filtrate concentrated under high vacuum

Sources & evidence

ORD record
ord-6e19fe14b5e54f6290f575841c691bff
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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