Triethylamine → HCID 23353495, compound

HRID 235116Notes

Reaction equation

HRID 235116 reaction equation
[NH2:1][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(N(CC)CC)C.[CH:26]([Si:29]([CH:43]([CH3:45])[CH3:44])([CH:40]([CH3:42])[CH3:41])[O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=1)([CH3:28])[CH3:27]>C(#N)C.C(Cl)Cl>[CH:43]([Si:29]([CH:26]([CH3:28])[CH3:27])([CH:40]([CH3:42])[CH3:41])[O:30][C:31]1[CH:39]=[CH:38][C:34]([C:35]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)=[O:36])=[CH:33][CH:32]=1)([CH3:45])[CH3:44]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene2×HCID 23353508HCID 23353508, compound2×

Product 1

HCID 23353495HCID 23353495, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.118 g, 0.489 mmol) and triethylamine (0.13 mL, 0.98 mmol) in acetonitrile (10 mL) was chilled to 0° C. and 4-triisopropylsilyloxybenzoyl chloride (0.16 g, 0.51 mmol) dissolved in methylene chloride was added all at once. The mixture was gently refluxed overnight; then 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.038 g, 0.16 mmol), 4-triisopropylsilyloxybenzoyl chloride (0.5 g, 1.6 mmol), and triethylamine (0.13 mL, 0.93 mmol) were added. The reaction was refluxed for an additional 24 hours, cooled and the solvent was removed at reduced pressure. The residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate and stirred vigorously for 5 hours. The phases were separated and the organic layer was washed with brine, dried over calcium sulfate and concentrated to a tan foam which was purified by flash chromatography on silica gel (1×3.5 inches). Elution with 25% ethyl acetate/hexane removed unweighed recovered acid chloride. Continued elution with an ethyl acetate/hexane gradient of from 1:3 to 3:1 followed by 100% ethyl acetate gave 0.238 g of 7-(4-triisopropylsilyloxybenzamido)-1-(4-methyl-1-piperazinyl)-naphthalene as a viscous tan oil.

Workup

  1. additionwas added all at once
  2. temperatureThe reaction was refluxed for an additional 24 hours
  3. temperaturecooled
  4. customthe solvent was removed at reduced pressure
  5. customThe residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  6. customThe phases were separated
  7. washthe organic layer was washed with brine
  8. dry with materialdried over calcium sulfate
  9. concentrationconcentrated to a tan foam which
  10. customwas purified by flash chromatography on silica gel (1×3.5 inches)
  11. washElution with 25% ethyl acetate/hexane removed
  12. customunweighed recovered acid chloride
  13. washContinued elution with an ethyl acetate/hexane gradient of from 1:3 to 3:1

Sources & evidence

ORD record
ord-16f39efc36694c44a8ea400f8cc40958
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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