Triethylamine → (S)-N-(4-acetyl-2-methyl-1-piperazinyl)-4-fluorobenzamide

HRID 1596228Notes

Reaction equation

HRID 1596228 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([NH2:10])[CH2:6][C@@H:5]1C)(=[O:3])[CH3:2].[CH2:12](N(CC)CC)C.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>ClCCl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([NH:10][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=2)[C@@H:6]([CH3:12])[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 45086083(S)-1-acetyl-4-amino-2-methylpiperazine

Product 1

HCID 53710546(S)-N-(4-acetyl-2-methyl-1-piperazinyl)-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-acetyl-4-amino-2-methylpiperazine (320 mg) and triethylamine (0.57 ml) in dichloromethane (10 ml) was added 4-fluorobenzoyl chloride (0.27 ml) at 0° C. The mixture was stirred at ambient temperature for 3 hours, washed with water and brine. The organic layer was dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and chloroform (1:9) to give (S)-N-(4-acetyl-2-methyl-1-piperazinyl)-4-fluorobenzamide (50 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography
  5. washeluting with a mixture of methanol and chloroform (1:9)

Sources & evidence

ORD record
ord-547d275ffdf14c55b69ac328cd767cf5
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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