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4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine → T-2307 free base

HRID 43277
Notes
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Reaction equation

HRID 43277 reaction equation
[NH2:1][C:2](=[N:33]O)[C:3]1[CH:32]=[CH:31][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([NH2:28])=[N:26]O)=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1>C(O)(=O)C.C(OC(=O)C)(=O)C.[Pd]>[NH2:33][C:2](=[NH:1])[C:3]1[CH:32]=[CH:31][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]([C:25]([NH2:28])=[NH:26])=[CH:29][CH:30]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 730702114-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine

Product 1

HCID 9803135T-2307 free baseYield 61.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Into a suspension of 1.07 g of 4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-hydroxybenzamidine in 10 mL of acetic acid, 0.64 mL of acetic anhydride was added at room temperature, and the suspension was stirred at room temperature for 40 min. The mixture, after adding 0.10 g of 5% palladium on carbon, was stirred under hydrogen atmosphere for 2 hours 15 min. The mixture was filtered to remove insoluble matters, and after adding 4 mL of 6.0 mol/L hydrochloric acid, the mixture was filtered again to remove insoluble matters, and the solvent was removed by evaporation under reduced pressure. To the obtained residue, a 5.0 mol/L sodium hydroxide aqueous solution was added to adjust the pH to 12.5, then the solid matter was collected by filtration to obtain 0.61 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine as a white solid.

Workup

  1. additionwas added at room temperature
  2. stirringwas stirred under hydrogen atmosphere for 2 hours 15 min
  3. filtrationThe mixture was filtered
  4. customto remove insoluble matters
  5. additionafter adding 4 mL of 6.0 mol/L hydrochloric acid
  6. filtrationthe mixture was filtered again
  7. customto remove insoluble matters
  8. customthe solvent was removed by evaporation under reduced pressure
  9. additionTo the obtained residue, a 5.0 mol/L sodium hydroxide aqueous solution was added
  10. filtrationthe solid matter was collected by filtration

Sources & evidence

ORD record
ord-122d027bc0c542fea0717219748a2df5
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536343B2

Reaction notes

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