2-Dimethylaminopyridine → 1-(4-fluorobenzyl)-4-(1H-imidazol-1-ylcarbonyl)piperazin-2-one

HRID 1162800Notes

Reaction equation

HRID 1162800 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[C:16](N1C=CN=C1)([N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)=[O:17].CN(C1C=CC=CN=1)C>CC#N>[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:16]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)=[O:17])[CH2:9][C:8]2=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 185386381-(4-Fluorobenzyl)piperazin-2-one

Product 1

HCID 684328121-(4-fluorobenzyl)-4-(1H-imidazol-1-ylcarbonyl)piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)piperazin-2-one (2.17 grams, 10.4 mmol) in 50 ml MeCN was added 1,1′-carbonyldiimidazole (2.03 g, 12.5 mmol) and dimethylaminopyridine (64 mg, 0.52 mmol). The solution was stirred at room temperature for 1 hour, concentrated under vacuum, and then dissolved in a mixture of CH2Cl2/CHCl3. The organic solution was washed with water three times, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was triturated with diethyl ether, and filtered to provide the title product as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.27 (t, J=6.9 Hz, 2H), 7.21 (t, J=1.4 Hz, 1H), 7.13 (s, 1H), 7.05 (t, J=8.6 Hz, 2H), 4.60 (s, 2H), 4.34 (s, 2H), 3.80 (t, J=5.4 Hz, 2H), 3.40 (t, J=5.4 Hz, 2H); ES MS (M+1)=303.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutiondissolved in a mixture of CH2Cl2/CHCl3
  3. washThe organic solution was washed with water three times
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-ad23458d707e452b97e106487c693372
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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