Dichloromethane → N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-4-hydroxy-1,2-benzenediamine

HRID 395817Notes

Reaction equation

HRID 395817 reaction equation
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:32]2[C:36](=[O:37])[C:35]3=[CH:38][CH:39]=CC=[C:34]3[C:33]2=O)=[C:13]([CH:31]=1)[NH:14][C:15]([O:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22](C2C=CN=CC=2)[CH2:21][CH2:20]1)=[O:16])(C(C)(C)C)(C)C.[CH2:43]([Cl:45])Cl>NN.CO>[Cl:45][C:43]1[CH:39]=[CH:38][C:35]([C:36]([NH:32][C:12]2[C:13]([NH:14][C:15]([O:17][CH:18]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:19]3[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=3)=[O:16])=[CH:31][C:9]([OH:8])=[CH:10][CH:11]=2)=[O:37])=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 181745295-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

Product 1

HCID 86585764N1-(4-Chlorobenzoyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-4-hydroxy-1,2-benzenediamineYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 9321HydrazineSolvent

Procedure

A solution of 5-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline (1.34 g, 2.28 mmol) in 1 M hydrazine in methanol (6 mL) was stirred at ambient temperature for 40 h during which time a white precipitate formed. The mixture was further diluted with methylene chloride and cooled with an ice bath then filtered. The filtrate was washed once with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield 890 mg (86%) of the title compound as a tan powder.

Workup

  1. customformed
  2. temperaturecooled with an ice bath
  3. filtrationthen filtered
  4. washThe filtrate was washed once with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a4b86d1e0e340769a73a4abe3ca894e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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