Acetic Anhydride → T-2307 free base

HRID 644134Notes

Reaction equation

HRID 644134 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(OC(=O)C)(=O)C>[C].[Pd].C(O)(=O)C>[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

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 730702114-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine

Product 1

HCID 9803135T-2307 free baseYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To an acetic acid (150 mL) suspension of 14.9 g of 4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-hydroxybenzamidine was added 5.97 mL of acetic anhydride at room temperature, which was then stirred at room temperature for 1 hour and 20 minutes. To this mixture was added 1.50 g of 5% palladium-carbon, which was then stirred under hydrogen atmosphere for 4 hours and 40 minutes. Insoluble matter was filtered off, and 55 mL of 6.0 mol/L hydrochloric acid was then added. The solvent was distilled off under reduced pressure, and ethanol was added to the resultant residue. The solid matter was collected by filtration to provide 14.0 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine as white solid form.

Workup

  1. stirringwas then stirred under hydrogen atmosphere for 4 hours and 40 minutes
  2. filtrationInsoluble matter was filtered off
  3. addition55 mL of 6.0 mol/L hydrochloric acid was then added
  4. distillationThe solvent was distilled off under reduced pressure, and ethanol
  5. additionwas added to the resultant residue
  6. filtrationThe solid matter was collected by filtration

Sources & evidence

ORD record
ord-f06094f92f32469b932e2d692afac5be
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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