Benzoyl chloride → 7-Benzoyloxy-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235139Notes

Reaction equation

HRID 235139 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[C:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chloride2×HCID 108002178-(4-Methylpiperazin-1-yl)naphthalen-2-ol

Product 1

HCID 233534937-Benzoyloxy-1-(4-methyl-1-piperazinyl)-naphthalene

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 7-hydroxy-1-(4-methyl-1-piperazinyl)-naphthalene (0.065 g, 0.268 mmol) and benzoyl chloride (0.035 mL, 0.302 mmol) in methylene chloride (1 mL) and saturated sodium bicarbonate (1 mL) was stirred at room temperature. After several hours, a second equivalent of benzoyl chloride was added with continued stirring overnight. The reaction was diluted with ethyl acetate and the phases were separated. The organic layer was washed with 1N sodium hydroxide, water and brine; then it was dried over magnesium sulfate and concentrated to an oil which solidified (0.065 g, 69%). A sample recrystallized from ether/hexane as a light pink solid was submitted for analysis: mp 82°-82.5° C. Analysis calculated for C22H22N2O2 ·0.25 H2O: C, 75.30; H, 6.46; N, 7.98. Found: C, 75.51; H, 6.29; N, 7.97.

Workup

  1. waitAfter several hours
  2. stirringwith continued stirring overnight
  3. customthe phases were separated
  4. washThe organic layer was washed with 1N sodium hydroxide, water and brine
  5. dry with materialthen it was dried over magnesium sulfate
  6. concentrationconcentrated to an oil which
  7. customA sample recrystallized from ether/hexane as a light pink solid

Sources & evidence

ORD record
ord-26e64627724a45acbebc8e65a82dac40
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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