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

HRID 427667Notes

Reaction equation

HRID 427667 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-63a6817861734f2e9b226a4cf5e4d2d3
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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