Acetic Anhydride → HCID 86625854, compound

HRID 644149Notes

Reaction equation

HRID 644149 reaction equation
[NH2:1][C:2](=[N:32][OH:33])[C:3]1[CH:31]=[CH:30][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:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>C(O)(=O)C>[NH2:1][C:2](=[N:32][O:33][C:34](=[O:36])[CH3:35])[C:3]1[CH:31]=[CH:30][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]([NH2:27])=[O:26])=[CH:28][CH:29]=3)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86625843HCID 86625843, compound

Product 1

HCID 86625854HCID 86625854, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To an acetic acid (15 mL) suspension of 1.00 g of 4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=oxime was added 0.48 mL of acetic anhydride at room temperature, which was then stirred at the same temperature for one hour. The solvent was distilled off under reduced pressure, and the resultant residue was subsequently added to a mixture of water and chloroform, which was then adjusted to pH 7.5 using a saturated sodium bicarbonate aqueous solution. The precipitate was collected by filtration and washed with water and chloroform to provide 1.07 g of 4-{3-[4-(3-{4-[amino(acetyloxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamide=O-acetyloxime as white solid form.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionthe resultant residue was subsequently added to a mixture of water and chloroform, which
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and chloroform

Sources & evidence

ORD record
ord-ab006dd2445345519f67bb113ab82e1b
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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