5-(tert-butyldimethylsilyloxy)-2-phthalimido-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline → 4-(tert-Butyldimethyl-silyloxy)-N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamine

HRID 2301838Notes

Reaction equation

HRID 2301838 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:32]2C(=O)C3=CC=CC=C3C2=O)=[C:13]([CH:31]=1)[NH:14][C:15]([O:17][CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>NN.CO.C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:31]=[C:13]([NH:14][C:15]([O:17][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[CH2:21][CH2:20]2)=[O:16])[C:12]([NH2:32])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 1

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

Product 1

HCID 538609714-(tert-Butyldimethyl-silyloxy)-N2-[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl-1,2-benzenediamineYield 86%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 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-f907f14439004aa5a9f5d305fa44bc13
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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