Hydrochloric Acid → 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine

HRID 644148Notes

Reaction equation

HRID 644148 reaction equation
[NH2:1][C:2](=[N:33]C(=O)[O-])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([NH2:32])=[N:30][OH:31])=[CH:25][CH:24]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Cl>C(O)C>[NH2:33][C:2](=[NH:1])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][C:26]([C:29]([NH2:32])=[N:30][OH:31])=[CH:27][CH:28]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86625852HCID 86625852, compound

Product 1

HCID 722646604-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N'-hydroxybenzamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (5 mL) suspension of 0.50 g of tert-butyl=[1-amino-1-(4-{3-[1-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-4-piperidinyl]propoxy}phenyl)methylidene]carbamate was added 1 mL of hydrochloric acid at room temperature, which was then stirred at the same temperature for 15 hours and 30 minutes. To the reaction mixture was added 4 mL of hydrochloric acid at room temperature, which was then stirred at the same temperature for 2 hours and 30 minutes. The solvent was distilled off under reduced pressure, and water was then added, followed by adjustment to pH 12.5 using a 5 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water. The resultant solid was dissolved in 1 mol/L hydrochloric acid, followed by distilling off the solvent under reduced pressure before purification using silica gel column chromatography (silica gel: ODS-A from YMC, eluent; water:ethanol=95:5). The eluate was concentrated to about 20 mL, which was then adjusted to pH 12.5 using a 5 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water to provide 0.17 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}-N′-hydroxybenzamidine as white solid form.

Workup

  1. stirringwhich was then stirred at the same temperature for 2 hours and 30 minutes
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas then added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dissolutionThe resultant solid was dissolved in 1 mol/L hydrochloric acid
  7. distillationby distilling off the solvent under reduced pressure
  8. custombefore purification
  9. concentrationThe eluate was concentrated to about 20 mL, which
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with water

Sources & evidence

ORD record
ord-9e86d22c1cb146309562d1a60fdae5d4
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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