Potassium Carbonate → HCID 21911719, compound

HRID 1245359Notes

Reaction equation

HRID 1245359 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:14])[CH2:11][CH2:12]Br.[C:15]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:14])[CH2:11][CH2:12][N:28]1[CH2:27][CH2:26][N:25]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 643495Benzyl piperazine-1-carboxylateHCID 2781531HCID 2781531, compound

Product 1

HCID 21911719HCID 21911719, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of N-(2,6-dimethylphenyl)-3-bromopropanamide (1 g, 4.5 mmol) and N-carbobenzyloxypiperazine (1,7 g, 6.8 mmol) in 10mL of acetone was added potassium carbonate (0.93 g, 6.8 mmol). The mixture was refluxed for 24 hours. The mixture was filtered, and the solvent was removed from the filtrate under reduced pressure. The residue was purified using column chromatography, to provide N-(2,6-dimethylphenyl)-3-(4-carbobenzyloxypiperazinyl)propanamide, a compound of formula (3). B. To N-(2,6dimethylphenyl)-3-(4carbobenzyloxypiperanzinyl)propanamide (1.3 g) in 10 mL of methanol was added 10% Pd/C, and the mixture was hydrogenated at 30 psi for 24 hours. The mixture was filtered, and the solvent was removed from the filtrate under reduced pressure, to afford N-(2,6-dimethylphenyl)-3-piperazinylpropanamide, a compound of formula (4),which was used without further purification. C. A mixture of N-(2,6dimethylphenyl)-3-piperazinylpropanamide (0.15 g, 0.57 mmol) and 2-methyl-5-(oxiran-2-ylmethoxy)benzothiazole (0.127 g, 0.57 mmol) in 8 mL of ethanol was refluxed for 24 hours. The solvent was removed under reduced pressure, and the residue was purified using preparative TLC.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed from the filtrate under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-d976f8e3d1ad4249964f800bd2c96a9a
Source dataset
uspto-grants-2006_10
Patent number
US07125876B2

Reaction notes

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